Polarizing devices and methods of making the same

ABSTRACT

Certain, non-limiting embodiments of the disclosure provide ophthalmic elements and devices comprising an at least partial coating adapted to polarize at least transmitted radiation on at least a portion of at least one exterior surface of an ophthalmic element or substrate. Further, according to certain non-limiting embodiments, the at least partial coating adapted to polarize at least transmitted radiation comprises at least one at least partially aligned dichroic material. Other non-limiting embodiments of the disclosure provide methods of making ophthalmic elements and devices comprising forming an at least partial coating adapted to polarize at least transmitted radiation on at least a portion of at least one exterior surface of the ophthalmic element or substrate. Optical elements and devices and method of making the same are also disclosed.

CROSS-REFERENCE TO RELATED APPLICATIONS

Not applicable.

STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH OR DEVELOPMENT

Not applicable.

REFERENCE TO A SEQUENCE LISTING

Not applicable.

BACKGROUND

Polarizing ophthalmic devices, such as polarizing sunglasses, can reduceglare due to light reflected off surfaces, such as but not limited topavement, water, and snow, thereby enhancing vision under glareconditions. Consequently, polarizing ophthalmic devices have become ofincreasing interest for use in sports and other outdoor activities inwhich reflected glare can be problematic.

Conventional polarizing filters for ophthalmic devices are formed fromsheets or layers of a polymeric material that has been stretched orotherwise oriented and impregnated with an iodine chromophore ordichroic dye. For example, one method of forming a conventionalpolarizing filter for ophthalmic devices is to heat a sheet or layer ofpolyvinyl alcohol (“PVA”) to soften the PVA and then stretch the sheetto orient the PVA polymer chains. Thereafter, an iodine chromophore ordichroic dye is impregnated into the sheet such that the iodine or dyemolecules attach to the aligned polymer chains and take on a particularorder or alignment. Alternatively, the iodine chromophore or thedichroic dye can be first impregnated into the PVA sheet, and thereafterthe sheet can be heated and stretched as described above to orient thePVA polymer chains and associated chromophore or dye.

Iodine chromophores and dichroic dyes are dichroic materials, that is,they absorb one of two orthogonal plane-polarized components oftransmitted radiation more strongly than the other. Although dichroicmaterials will preferentially absorb one of two orthogonalplane-polarized components of transmitted radiation, if the molecules ofthe dichroic material are not suitably positioned or arranged, no netpolarization of transmitted radiation will be achieved. That is, due tothe random positioning of the molecules of the dichroic material, theselective absorption by the individual molecules will cancel each othersuch that no net or overall polarizing effect is achieved. However, bysuitably positioning or arranging the molecules of the dichroic materialwithin the oriented polymer chains of the PVA sheet, a net polarizationcan be achieved. That is, the PVA sheet can be made to polarizetransmitted radiation, or in other words, a polarizing filter can beformed. As used herein, the term “polarize” means to confine thevibrations of the electric vector of light waves to one direction.

One method of forming a polarizing ophthalmic device utilizing suchpolarizing polymer sheet filters is to laminate or glue the filter tothe convex outer surface of a lens substrate. Another method of forminglenses utilizing conventional polarizing polymer sheet filters involveslining the surface of a lens mold with the polarizing sheet andsubsequently filling the mold with the substrate material such that thepolarizing sheet is on the surface of the lens when removed from themold. Still other methods involve the incorporation of the filter intothe lens structure itself. For example, the filter can be incorporatedinto the lens structure by laminating the filter between two substratesthat together form the lens, or by casting a substrate material aroundthe filter. In the latter method, the polarizing filter can be placedinto a mold and the mold filled with the substrate material, typically athermosetting plastic monomer, such that the substrate materialsurrounds and encapsulates the polarizing filter. Thereafter, thesubstrate material can be cured to form the lens.

It is also known to form a polarizing layer by forming a film of alinear photo-polymerizable material exhibiting selective orientation ona release layer component of a transfer foil. Thereafter, a liquidcrystal polymer material containing a dichroic dye can be applied to thelinear photo-polymerizable material and the chains of the liquid crystalpolymer aligned. Since a dichroic dye is contained within the liquidcrystal polymer, when the liquid crystal polymer chains are aligned, thedichroic dye molecules are also aligned and a net polarization effectcan be achieved. The polarizing layer can then be transferred from thetransfer foil to a suitable substrate by, for example, hot stamping.

Other methods of forming polarizing sheets or layers using liquidcrystal materials are also known. For example, polarizing sheets formedfrom oriented thermotropic liquid crystal films containing dichroic dyeshave been disclosed. Further, polarizing sheets formed by extrudingliquid crystalline polymers that contain dichroic dyes covalently linkedas part of the main polymer chains have been disclosed.

SUMMARY

Various non-limiting embodiments disclosed herein provide opticalelements and devices and ophthalmic elements and devices. For example,one non-limiting embodiment provides an ophthalmic element comprising anat least partial coating adapted to polarize at least transmittedradiation on at least a portion of at least one exterior surface of theophthalmic element.

Another non-limiting embodiment provides an ophthalmic elementcomprising at least one orientation facility on at least a portion of atleast one exterior surface of the ophthalmic element, and an at leastpartial coating adapted to polarize at least transmitted radiation on atleast a portion of the at least one orientation facility.

Another non-limiting embodiment provides an ophthalmic elementcomprising at least one at least partial coating comprising an alignmentmedium on at least a portion of at least one exterior surface of theophthalmic element, at least one at least partial coating comprising analignment transfer material on at least a portion of the at least one atleast partial coating comprising the alignment medium, and at least oneat least partial coating comprising an anisotropic material and at leastone dichroic material on at least a portion of the at least one at leastpartial coating comprising the alignment transfer material.

Still another non-limiting embodiment provides an ophthalmic elementcomprising a substrate, at least one orientation facility comprising anat least partial coating comprising a photo-orientable polymer networkon at least a portion of at least one exterior surface of the substrate,and an at least partial coating adapted to polarize at least transmittedradiation on at least a portion of the at least one at least partialcoating comprising the photo-orientable polymer network, the at leastpartial coating adapted to polarize at least transmitted radiationcomprising a liquid crystal polymer and at least one dichroic dye.

Yet another non-limiting embodiment provides an optical elementcomprising an at least partial coating adapted to polarize at leasttransmitted radiation on at least a portion of at least one exteriorsurface of the optical element, the at least partial coating comprisingan at least partially ordered liquid crystal material and at least oneat least partially aligned dichroic material.

Another non-limiting embodiment provides an optical device comprising atleast one optical element comprising an at least partial coatingcomprising an alignment medium on at least a portion of at least oneexterior surface of the at least one optical element, and an at leastpartial coating comprising an anisotropic material and at least onedichroic material on at least a portion of the at least one at leastpartial coating comprising the alignment medium.

Other non-limiting embodiments disclosed herein provide methods ofmaking optical elements and ophthalmic elements. For example, onenon-limiting embodiment provides a method of making an ophthalmicelement comprising forming an at least partial coating adapted topolarize at least transmitted radiation on at least a portion of atleast one exterior surface of the ophthalmic element.

Another non-limiting embodiment provides a method of making anophthalmic element comprising imparting at least one orientationfacility comprising an at least partial coating comprising an alignmentmedium on at least a portion of at least one exterior surface of theophthalmic element, applying at least one dichroic material to at leasta portion of the at least one orientation facility, and at leastpartially aligning at least a portion of the at least one dichroicmaterial.

Another non-limiting embodiment provides a method of making anophthalmic element comprising applying an at least partial coating to atleast a portion of at least one exterior surface of the ophthalmicelement, and adapting at least a portion of the at least partial coatingto polarize at least transmitted radiation.

Still another non-limiting embodiment provides a method of making anophthalmic element comprising applying an at least partial coatingcomprising an alignment medium to at least a portion of at least oneexterior surface of the ophthalmic element, at least partially orderingat least a portion of the alignment medium, applying an at least partialcoating comprising an anisotropic material and at least one dichroicmaterial to at least a portion of the at least partial coatingcomprising the at least partially ordered alignment medium, and at leastpartially aligning at least a portion of the at least one dichroicmaterial.

Another non-limiting embodiment provides a method of making a lens forophthalmic applications comprising applying an at least partial coatingcomprising a photo-orientable polymer network to at least a portion ofat least one exterior surface of a lens, at least partially ordering atleast a portion of the photo-orientable polymer network withplane-polarized ultraviolet radiation, applying an at least partialcoating comprising a liquid crystal material and at least one dichroicdye to at least a portion of the at least one at least partial coatingcomprising the photo-orientable polymer network, at least partiallyaligning at least a portion of the at least partial coating comprisingthe liquid crystal material and the at least one dichroic dye, and atleast partially setting at least a portion of the coating comprising theliquid crystal polymer and the at least one dichroic dye.

Still another non-limiting embodiment provides a method of making anoptical element comprising applying an at least partial coating to atleast a portion of at least one exterior surface of the optical element,and adapting at least a portion of the at least partial coating topolarize at least transmitted radiation.

DETAILED DESCRIPTION

As used in this specification and the appended claims, the articles “a,”“an,” and “the” include plural referents unless expressly andunequivocally limited to one referent.

Additionally, for the purposes of this specification, unless otherwiseindicated, all numbers expressing quantities of ingredients, reactionconditions, and other properties or parameters used in the specificationare to be understood as being modified in all instances by the term“about.” Accordingly, unless otherwise indicated, it should beunderstood that the numerical parameters set forth in the followingspecification and attached claims are approximations. At the very least,and not as an attempt to limit the application of the doctrine ofequivalents to the scope of the claims, numerical parameters should beread in light of the number of reported significant digits and theapplication of ordinary rounding techniques.

Further, while the numerical ranges and parameters setting forth thebroad scope of the invention are approximations as discussed above, thenumerical values set forth in the Examples section are reported asprecisely as possible. It should be understood, however, that suchnumerical values inherently contain certain errors resulting from themeasurement equipment and/or measurement technique.

Elements and devices according to various non-limiting embodiments ofthe present invention will now be described. One non-limiting embodimentprovides an optical element, and more specifically provides anophthalmic element comprising an at least partial coating adapted topolarize at least transmitted radiation on at least a portion of atleast one exterior surface of the ophthalmic element.

As previously discussed, “polarize” means to confine the vibrations ofthe electric vector of light waves to one direction. Further aspreviously discussed, conventional polarizing ophthalmic elements, suchas lenses for ophthalmic devices, are typically formed by laminating ormolding a polarizing filter formed from a stretched PVA sheet (or layer)containing a dichroic material, such as an iodine chromophore, to a lenssubstrate. However, according various non-limiting embodiments disclosedherein, the ophthalmic element comprises an at least partial coatingadapted to polarize at least transmitted radiation on at least a portionof at least one exterior surface of the ophthalmic element. Thus,according to these non-limiting embodiments, the conventional laminatestructure discussed above is not required. As used herein thepreposition “on” means that the subject coating is directly connected tothe object surface or indirectly connected to the object surface thoughone or more other coatings or structures. Further, as used herein theterm “coating” means a film, which may or may not have a uniformthickness, and specifically excludes the stretched polymer sheets of theprior art.

The term “ophthalmic” as used herein refers to elements and devices thatare associated with the eye and vision, such as, but not limited to,lenses for eyewear, and eyewear. Thus, for example, according to variousnon-limiting embodiments disclosed herein, the ophthalmic element can bechosen from corrective lenses, non-corrective lenses, and magnifyinglenses.

Further, the ophthalmic elements according to various non-limitingembodiments disclosed herein can be formed from any suitable substratematerial, including but not limited to, glasses and organic materials.

For example, according to various non-limiting embodiments disclosedherein, the ophthalmic element can be formed from an organic substratematerial. Suitable organic substrate materials for use in conjunctionwith various non-limiting embodiments disclosed herein include, but arenot limited to, the art-recognized polymers that are useful asophthalmic elements, e.g., organic optical resins that are used toprepare optically clear castings for optical applications, such asophthalmic lenses.

Specific, non-limiting examples of organic substrate materials that maybe used to form the ophthalmic elements disclosed herein includepolymeric materials, for examples, homopolymers and copolymers, preparedfrom the monomers and mixtures of monomers disclosed in U.S. Pat. No.5,962,617 and in U.S. Pat. No. 5,658,501 from column 15, line 28 tocolumn 16, line 17, the disclosures of which U.S. patents arespecifically incorporated herein by reference. For example, suchpolymeric materials can be thermoplastic or thermoset polymericmaterials, can be transparent or optically clear, and can have anyrefractive index required. Non-limiting examples of such disclosedmonomers and polymers include: polyol(allyl carbonate) monomers, e.g.,allyl diglycol carbonates such as diethylene glycol bis(allylcarbonate), which monomer is sold under the trademark CR-39 by PPGIndustries, Inc.; poly(urea urethane) polymers, which are prepared, forexample, by the reaction of a polyurethane prepolymer and a diaminecuring agent, a composition for one such polymer being sold under thetrademark TRIVEX by PPG Industries, Inc.; polyol(meth)acryloylterminated carbonate monomer; diethylene glycol dimethacrylate monomers;ethoxylated phenol methacrylate monomers; diisopropenyl benzenemonomers; ethoxylated trimethylol propane triacrylate monomers; ethyleneglycol bismethacrylate monomers; poly(ethylene glycol) bismethacrylatemonomers; urethane acrylate monomers; poly(ethoxylated bisphenol Adimethacrylate); poly(vinyl acetate); poly(vinyl alcohol); poly(vinylchloride); poly(vinylidene chloride); polyethylene; polypropylene;polyurethanes; polythiourethanes; thermoplastic polycarbonates, such asthe carbonate-linked resin derived from bisphenol A and phosgene, onesuch material being sold under the trademark LEXAN; polyesters, such asthe material sold under the trademark MYLAR; poly(ethyleneterephthalate); polyvinyl butyral; poly(methyl methacrylate), such asthe material sold under the trademark PLEXIGLAS, and polymers preparedby reacting polyfunctional isocyanates with polythiols or polyepisulfidemonomers, either homopolymerized or co-and/or terpolymerized withpolythiols, polyisocyanates, polyisothiocyanates and optionallyethylenically unsaturated monomers or halogenated aromatic-containingvinyl monomers. Also contemplated are copolymers of such monomers andblends of the described polymers and copolymers with other polymers, forexample, to form block copolymers. While, the exact nature of theorganic substrate material is not critical to various non-limitingembodiments disclosed herein, in one non-limiting embodiment, theorganic substrate material should be chemically compatible with the atleast partial coatings adapted to polarize at least transmittedradiation on at least a portion of at least one exterior surface of theophthalmic element.

Further, according to certain non-limiting embodiments disclosed herein,the substrates forming the ophthalmic elements may have a protectivecoating, such as, but not limited to, an abrasion-resistant coating,such as a “hard coat,” on their exterior surfaces. For example,commercially available thermoplastic polycarbonate lens substrates areoften sold with an abrasion-resistant coating already applied to theirexterior surfaces because these surfaces tend to be readily scratched,abraded or scuffed. An example of such a lens substrate is the GENTEX™polycarbonate lens (available from Gentex Optics). Therefore, as usedherein the term “substrate” includes a substrate having an protectivecoating, such as but not limited to an abrasion-resistant coating, onits surface(s).

Still further, the ophthalmic elements and substrates used to form theophthalmic elements according to various non-limiting embodimentsdisclosed herein can be untinted, tinted, photochromic, ortinted-photochromic ophthalmic elements.

As used herein the term “untinted” with respect to ophthalmic elementsand substrates means essentially free of coloring agent additions (suchas, but not limited to, conventional dyes) and having an absorptionspectrum for visible radiation that does not vary significantly inresponse to actinic radiation. As used herein “actinic radiation” meanselectromagnetic radiation that is capable of causing a response.Although not limiting herein, actinic radiation can include both visibleand ultraviolet radiation.

As used herein the term “tinted” with respect to ophthalmic elements andsubstrates means containing a coloring agent addition (such as, but notlimited to, conventional dyes) and having an absorption spectrum forvisible radiation that does not vary significantly in response toactinic radiation.

As used herein the term “photochromic” means having an absorptionspectrum for visible radiation that varies in response to at leastactinic radiation and is thermally reversible. Although not limitingherein, for example, photochromic elements, substrates, coatings, andmaterials that can be used in conjunction with various non-limitingembodiments disclosed herein may change from a clear state to coloredstate in response radiation, or they may change from one colored stateto another colored state in response to radiation. For example, in onenon-limiting embodiment the photochromic ophthalmic element may changefrom a clear state to a colored state in response to actinic radiationand revert back to the clear state in response to thermal radiation orheat. Alternatively, the photochromic ophthalmic element may change froma first colored state to a second colored state in response to actinicradiation and revert back to the first color state in response tothermal radiation or heat.

As used herein the term “tinted-photochromic” with respect to theophthalmic elements and substrates means containing a coloring agentaddition and a photochromic material, and having an absorption spectrumfor visible radiation that varies in response to at least actinicradiation and is thermally reversible. Thus for example, in onenon-limiting embodiment, the tinted-photochromic substrate can have afirst color characteristic of the coloring agent and a second colorcharacteristic of the combination of the coloring agent the photochromicmaterial when exposed to actinic radiation.

As discussed above, the ophthalmic elements according to variousnon-limiting embodiments disclosed herein comprise an at least partialcoating adapted to polarize at least transmitted radiation on at least aportion of at least one exterior surface of the ophthalmic elements. Asused herein the term “transmitted radiation” refers to radiation that ispassed through at least a portion of an element or substrate. Althoughnot limiting herein, the transmitted radiation can be visible radiationor can be a combination of visible radiation and ultraviolet radiation.According to various non-limiting embodiments disclosed herein, the atleast partial coating can be adapted to polarize transmitted visibleradiation, or it can be adapted to polarize a combination of transmittedvisible and transmitted ultraviolet radiation.

Further, the at least partial coating adapted to polarize at leasttransmitted radiation on at least a portion of at least one exteriorsurface of the ophthalmic element can comprise at least one dichroicmaterial. As used herein the terms “dichroic material” and “dichroicdye” refers to a material that absorbs one of two orthogonalplane-polarized components of at least transmitted radiation morestrongly than the other. One measure of how strongly the dichroicmaterial absorbs one of two orthogonal plane-polarized components is the“absorption ratio.” As used herein the term “absorption ratio” refers tothe ratio of the absorbance of radiation linearly polarized in a firstplane to the absorbance of the same wavelength radiation linearlypolarized in a plane orthogonal to the first plane, wherein the firstplane is taken as the plane with the highest absorbance. Methods ofdetermining absorption ratios are described in detail in the Examplessection below.

Dichroic materials that can be used in conjunction with variousnon-limiting embodiments disclosed herein include, but are not limitedto, dichroic materials having an absorption ratios ranging from 2 to 30(or higher as required). For example, according to certain non-limitingembodiments, the dichroic material can have an absorption ratio of atleast 3, at least 5, at least 7, at least 10 or greater. Further,combinations of dichroic materials having different absorption ratioscan be used in accordance with various non-limiting embodimentsdisclosed herein. For example, in one non-limiting embodiment, the atleast partial coating adapted to polarize at least transmitted radiationcan comprise a first dichroic material having a first absorption ratioand at least one second dichroic material having a second absorptionratio that is different than the first absorption ratio.

Non-limiting examples of dichroic materials that are suitable for use inconjunction with various non-limiting embodiments described hereininclude azomethines, indigoids, thioindigoids, merocyanines, indans,quinophthalonic dyes, perylenes, phthaloperines, triphenodioxazines,indoloquinoxalines, imidazo-triazines, tetrazines, azo and (poly)azodyes, benzoquinones, naphthoquinones, anthraquinone and(poly)anthraquinones, anthrapyrimidinones, iodine and iodates.

Although not limiting herein, in one non-limiting embodiment, thedichroic material is chosen from azo and poly(azo) dyes. In anothernon-limiting embodiment, the dichroic material is anthraquinones and(poly)anthraquinones.

Further, in another non-limiting embodiment, the dichroic material canbe a polymerizable dichroic material. That is, according to thisnon-limiting embodiment, the dichroic material can comprise at least onegroup that is capable of being polymerized (i.e., a “polymerizablegroup”). For example, although not limiting herein, in one non-limitingembodiment the at least one dichroic material can have at least onealkoxy, polyalkoxy, alkyl, or polyalkyl substituent terminated with atleast one polymerizable group.

According to one non-limiting embodiment, the at least partial coatingadapted to polarize at least transmitted radiation on at least a portionof at least one exterior surface of the ophthalmic element can compriseat least one dichroic material and at least one anisotropic material. Asused herein the term “anisotropic” means having at least one propertythat differs in value when measured in at least one different direction.Thus, “anisotropic materials” are materials that have at least oneproperty that differs in value when measured in at least one differentdirection. For example, although not limiting herein, the anisotropicmaterials that can be used in conjunction with various non-limitingembodiments disclosed herein can be optically anisotropic materials.

Non-limiting examples of anisotropic materials that are suitable for usein conjunction with various non-limiting embodiments disclosed hereininclude liquid crystal materials chosen from liquid crystal polymers,liquid crystal pre-polymers, and liquid crystal monomers. As used hereinthe term “pre-polymer” means partially polymerized materials. Forexample, according one non-limiting embodiment, the at least partialcoating adapted to polarize at least transmitted radiation on at least aportion of at least one exterior surface of the ophthalmic element cancomprise at least one dichroic material and at least one anisotropicmaterial chosen from liquid crystal polymers, liquid crystalpre-polymers, and liquid crystal monomers.

Liquid crystal monomers that are suitable for use as anisotropicmaterials in conjunction with various non-limiting embodiments disclosedherein include mono-functional as well as multi-functional liquidcrystal monomers. Further, according to various non-limiting embodimentsdisclosed herein, the liquid crystal monomer can be a cross-linkableliquid crystal monomer, and can further be a photocross-linkable liquidcrystal monomer. As used herein the term “photocross-linkable” means amaterial, such as a monomer, a pre-polymer or a polymer, that can becross-linked on exposure to actinic radiation.

Non-limiting examples of cross-linkable liquid crystal monomers suitablefor use as anisotropic materials according to various non-limitingembodiments disclosed herein include liquid crystal monomers havingfunctional groups chosen from acrylates, methacrylates, allyl, allylethers, alkynes, amino, anhydrides, epoxides, hydroxides, isocyanates,blocked isocyanates, siloxanes, thiocyanates, thiols, urea, vinyl, vinylethers and blends thereof. Non-limiting examples of photocross-linkableliquid crystal monomers suitable for use as anisotropic materialsaccording to various non-limiting embodiments disclosed herein includeliquid crystal monomers having functional groups chosen from acrylates,methacrylates, alkynes, epoxides, thiols, and blends thereof.

Liquid crystal polymers and pre-polymers that are suitable for use asanisotropic materials in conjunction with various non-limitingembodiments disclosed herein include thermotropic liquid crystalpolymers and pre-polymers, and lyotropic liquid crystal polymers andpre-polymers. Further, the liquid crystal polymers and pre-polymers canbe main-chain polymers and pre-polymers or side-chain polymers andpre-polymers. Additionally, according to various non-limitingembodiments disclosed herein, the liquid crystal polymer or pre-polymercan be cross-linkable, and further can be photocross-linkable.

Non-limiting examples of suitable liquid crystal polymers andpre-polymers that are suitable for use as anisotropic materialsaccording to various non-limiting embodiments disclosed herein include,but are not limited to, main-chain and side-chain polymers andpre-polymers having functional groups chosen from acrylates,methacrylates, allyl, allyl ethers, alkynes, amino, anhydrides,epoxides, hydroxides, isocyanates, blocked isocyanates, siloxanes,thiocyanates, thiols, urea, vinyl, vinyl ethers, and blends thereof.Non-limiting examples of photocross-linkable liquid crystal polymers andpre-polymers that are suitable for use as anisotropic materialsaccording to various non-limiting embodiments disclosed herein includethose polymers and pre-polymers having functional groups chosen fromacrylates, methacrylates, alkynes, epoxides, thiols, and blends thereof.

Additionally, although not limiting herein, in accordance with variousnon-limiting embodiments, at least a portion of the anisotropic materialcan be at least partially ordered and at least a portion of the at leastone dichroic material can be at least partially aligned with at least aportion of the at least partially ordered anisotropic material. As usedherein the term “ordered” means brought into a suitable arrangement orposition, such as by alignment with another structure or by some otherforce or effect. Further, as used herein the term “aligned” meansbrought into suitable arrangement or position by interaction withanother structure.

As previously discussed, while dichroic materials absorb one of twoorthogonal plane-polarized components of transmitted radiation morestrongly than the other, the molecules of the dichroic material must besuitably positioned or arranged to achieve a net polarization oftransmitted radiation. Thus, according to various non-limitingembodiments disclosed herein, at least a portion of the at least onedichroic material can be brought into suitable position or arrangement(i.e., ordered or aligned) such that an overall polarization effect canbe achieved.

For example, in one non-limiting embodiment, the at least partialcoating can comprise an at least partially ordered anisotropic material(such as, but not limited to a liquid crystal material) and at least oneat least partially aligned dichroic material, wherein the at least oneat least partially aligned dichroic material is at least partiallyaligned with the at least partially ordered anisotropic material.Although not limiting herein, according to this non-limiting embodimentat least a portion of the at least one dichroic material can be at leastpartially aligned such that the long axis of the at least a portion ofthe at least one dichroic material is generally parallel to thedirection of the order of the anisotropic material.

In another non-limiting embodiment, the at least one dichroic materialcan bonded to or reacted with at least a portion of the anisotropicmaterial. For example, according to this non-limiting embodiment, the atleast one dichroic material can be polymerized into or reacted with atleast a portion of the anisotropic material. Further, although notlimiting herein, according to this non-limiting embodiment, the at leastone dichroic material can comprise at least one substituent containingterminal and/or pendant groups selected from hydroxyl, carboxyl,(meth)acryloxy, 2-(methacryloxy)ethylcarbamyl(—OC(O)NHC₂H₄OC(O)C(CH₃)═CH₂), epoxy or a mixture thereof.

In addition to the at least one dichroic material and the at least oneanisotropic material, the at least partial coating adapted to polarizeat least transmitted radiation on at least a portion of at least oneexterior surface of the ophthalmic element according to variousnon-limiting embodiments disclosed herein can further comprise at leastone photochromic material. As previously discussed, photochromicmaterials have an absorption spectrum that varies in response to atleast actinic radiation.

For example, although not limiting herein, the at least one photochromicmaterial can be chosen from pyrans, oxazines, fulgides and fulgimides,and metal dithizonates. However, according to various non-limitingembodiments, the particular photochromic material selected is notcritical, and its selection will depend on the ultimate application andthe color or hue desired for that application. In one non-limitingembodiment, the at least one photochromic material has at least oneabsorption maximum between 300 and 1000 nanometers when activated (i.e.exposed to actinic radiation).

Further, in some non-limiting embodiments, the at least partial coatingcan comprise a mixture of photochromic materials. Generally, althoughnot limiting herein, when two or more photochromic materials are used incombination, the photochromic materials are often chosen to complementone another to produce a desired color or hue. For example, mixtures ofphotochromic materials can be used according to certain non-limitingembodiments disclosed herein to attain certain activated colors, such asa near neutral gray or near neutral brown. See, for example, U.S. Pat.No. 5,645,767, column 12, line 66 to column 13, line 19, the disclosureof which is specifically incorporated by reference herein, whichdescribes the parameters that define neutral gray and brown colors.

Non-limiting examples of photochromic pyrans that can be used inconjunction with various non-limiting embodiments disclosed hereininclude benzopyrans, naphthopyrans, e.g., naphtho[1,2-b]pyrans,naphtho[2,1-b]pyrans, spiro-9-fluoreno[1,2-b]pyrans, phenanthropyrans,quinopyrans, and indeno-fused naphthopyrans, such as those disclosed inU.S. Pat. No. 5,645,767; spiropyrans, e.g.,spiro(benzindoline)naphthopyrans, spiro(indoline)benzopyrans,spiro(indoline)naphthopyrans, spiro(indoline)quinopyrans andspiro(indoline)pyrans; and heterocyclic-fused napthopyrans, such asthose disclosed in U.S. Pat. Nos. 5,723,072, 5,698,141, 6,153,126, and6,022,497, which are hereby incorporated by reference. More specificexamples of naphthopyrans and the complementary organic photochromicsubstances are described from column 11, line 57 through column 13, line36 in U.S. Pat. No. 5,658,501, which are hereby specificallyincorporated by reference herein.

Non-limiting examples of photochromic oxazines that can be used inconjunction with various non-limiting embodiments disclosed hereininclude benzoxazines, naphthoxazines, and spiro-oxazines, e.g.,spiro(indoline)naphthoxazines, spiro(indoline)pyridobenzoxazines,spiro(benzindoline)pyridobenzoxazines,spiro(benzindoline)naphthoxazines, spiro(indoline)benzoxazines, andspiro(indoline)fluoranthenoxazine.

Non-limiting examples of photochromic fulgides and fulgimides that canbe used in conjunction with various non-limiting embodiments disclosedherein include the 3-furyl and 3-thienyl fulgides and fulgimides, whichare at column 20, line 5 through column 21, line 38 in U.S. Pat. No.4,931,220 (which are hereby specifically incorporated by reference) andmixtures of any of the aforementioned photochromic materials/compounds.

Non-limiting examples of photochromic metal dithizonates that can beused in conjunction with various non-limiting embodiments disclosedherein include mercury dithizonates, which are described in, forexample, U.S. Pat. No. 3,361,706, which is hereby specificallyincorporated by reference herein.

In addition, it is contemplated that photochromic materials such asphotochromic dyes and photochromic compounds encapsulated in metaloxides may be used in accordance with various non-limiting embodimentsdisclosed herein. See, for example, the materials described in U.S. Pat.Nos. 4,166,043 and 4,367,170, which are hereby specifically incorporatedby reference herein. Additionally, polymerizable photochromic materials,such as those disclosed in U.S. Pat. No. 6,113,814, which is herebyspecifically incorporated by reference herein, and compatiblizedphotochromic materials, such as those disclosed in U.S. Pat. No.6,555,028, which is hereby specifically incorporated by referenceherein, can also be used in conjunction with various non-limitingembodiments disclosed herein.

Still further, according to various non-limiting embodiments disclosedherein, the at least partial coating adapted to polarize at leasttransmitted radiation can further comprise at least one additive thatmay facilitate one or more of the processing, the properties, or theperformance of the at least partial coating. Non-limiting examples ofsuch additives include dyes, alignment promoters, kinetic enhancingadditives, photoinitiators, solvents, light stabilizers (such as, butnot limited to, ultraviolet light absorbers and light stabilizers, suchas hindered amine light stabilizers (HALS)), heat stabilizers, moldrelease agents, rheology control agents, leveling agents (such as, butnot limited to, surfactants), free radical scavengers, and adhesionpromoters (such as hexanediol diacrylate and coupling agents). In onenon-limiting embodiment, the additive is a dye.

As used herein, the term “alignment promoter” means an additive that canfacilitate at least one of the rate and uniformity of the alignment of amaterial to which it is added. Non-limiting examples of alignmentpromoters that can be present in the at least partial coatings accordingto various non-limiting embodiments disclosed herein include thosedescribed in U.S. Pat. No. 6,338,808 and U.S. patent Publication Ser.No. 2002/0039627, which are hereby specifically incorporated byreference herein.

Non-limiting examples of dyes that can be present in the at leastpartial coating according to various non-limiting embodiments disclosedherein include organic dyes that are capable of imparting a desiredcolor or optical properties to the at least partial coating.

Non-limiting examples of kinetic enhancing additives that can be presentin the at least partial coating according to various non-limitingembodiments disclosed herein include epoxy-containing compounds, organicpolyols, and/or plastizers. More specific examples of such kineticenhancing additives are disclosed in U.S. Pat. No. 6,433,043 and U.S.patent Publication Ser. No. 2003/0045612, which are hereby specificallyincorporated by reference herein.

Non-limiting examples of photoinitiators that can be present in the atleast partial coating according to various non-limiting embodimentsdisclosed herein include cleavage-type photoinitators andabstraction-type photoinitators. Non-limiting examples of cleavage-typephotoinitiators include acetophenones, α-aminoalkylphenones, benzoinethers, benzoyl oximes, acylphosphine oxides and bisacylphosphine oxidesor mixtures of such initiators. A commercial example of such aphotoinitiator is DAROCURE® 4265, which is available from CibaChemicals, Inc. Non-limiting examples of abstraction-typephotoinitiators include benzophenone, Michler's ketone, thioxanthone,anthraquinone, camphorquinone, fluorone, ketocoumarin or mixtures ofsuch initiators.

Another non-limiting example of a photoinitiator that can be present inthe at least partial coating according to various non-limitingembodiments disclosed herein is a visible light photoinitiator.Non-limiting examples of suitable visible light photoinitiators are setforth at column 12, line 11 to column 13, line 21 of U.S. Pat. No.6,602,603, which are specifically incorporated by reference herein.

Non-limiting examples of solvents that can be present in the at leastpartial coating according to various non-limiting embodiments disclosedherein include those that will dissolve solid components of the coating,that are compatible with the coating and the ophthalmic elements andsubstrates, and/or can ensure uniform coverage of the exteriorsurface(s) to which the coating is applied. Potential solvents include,but are not limited to, the following: acetone, amyl propionate,anisole, benzene, butyl acetate, cyclohexane, dialkyl ethers of ethyleneglycol, e.g., diethylene glycol dimethyl ether and their derivates (soldas CELLOSOLVE® industrial solvents), diethylene glycol dibenzoate,dimethyl sulfoxide, dimethyl formamide, dimethoxybenzene, ethyl acetate,isopropyl alcohol, methyl cyclohexanone, cyclopentanone, methyl ethylketone, methyl isobutyl ketone, methyl propionate, propylene carbonate,tetrahydroduran, toluene, xylene, 2-methoxyethyl ether, 3-propyleneglycol methyl ether, and mixtures thereof.

The ophthalmic elements according to various non-limiting embodimentsdisclosed herein can further comprise one or more other coatings thatcan facilitate bonding, adhering, or wetting of the at least partialcoating adapted to polarize at least transmitted radiation on the atleast a portion of the at least one exterior surface of the ophthalmicelements. For example, the ophthalmic elements according to onenon-limiting embodiment can comprise an at least partial primer coatingbetween at least a portion of the at least partial coating adapted topolarize at least transmitted radiation and at least a portion of the atleast one exterior surface of the ophthalmic elements. Further, althoughnot required, according to this non-limiting embodiment, the primercoating can serve as a barrier coating to prevent interaction of thecoating ingredients with the ophthalmic element or substrate surface andvice versa.

Non-limiting examples of primer coatings that can be used in conjunctionwith various non-limiting embodiments disclosed herein include coatingscomprising coupling agents, at least partial hydrolysates of couplingagents, and mixtures thereof. As used herein “coupling agent” is means amaterial having at least one group capable of reacting, binding and/orassociating with a group on at least one surface. In one non-limitingembodiment, a coupling agent can serve as a molecular bridge at theinterface of at least two surfaces that can be similar or dissimilarsurfaces. Coupling agents, in another non-limiting embodiment, can bemonomers, oligomers and/or polymers. Such materials include, but are notlimited to, organo-metallics such as silanes, titanates, zirconates,aluminates, zirconium aluminates, hydrolysates thereof and mixturesthereof. As used herein the phrase “at least partial hydrolysates ofcoupling agents” means that at least some to all of the hydrolyzablegroups on the coupling agent are hydrolyzed. In addition to couplingagents and/or hydrolysates of coupling agents, the primer coatings cancomprise other adhesion enhancing ingredients. For example, although notlimiting herein, the primer coating can further comprise anadhesion-enhancing amount of an epoxy-containing material.Adhesion-enhancing amounts of an epoxy-containing materials when addedto the coupling agent containing coating composition can improve theadhesion of a subsequently applied coating as compared to a couplingagent containing coating composition that is essentially free of theepoxy-containing material. Other non-limiting examples of primercoatings that are suitable for use in conjunction with the variousnon-limiting embodiments disclosed herein include those described U.S.Pat. No. 6,602,603 and U.S. Pat. No. 6,150,430, which are herebyspecifically incorporated by reference.

Further, the ophthalmic elements according various non-limitingembodiments disclosed herein can further comprise at least oneadditional at least partial coating chosen from photochromic coatings,anti-reflective coatings, transitional coatings, primer coatings, andprotective coatings on at least a portion of the ophthalmic element. Forexample, although not limiting herein, the at least one additional atleast partial coating can be on at least a portion of the at leastpartial coating adapted to polarize at least transmitted radiation,i.e., as an overcoat. Additionally or alternatively, the at leastpartial coating adapted to polarize radiation can be on at least aportion of a first exterior surface of the ophthalmic element, and theat least one additional at least partial coating can be on at least aportion of a second exterior surface of the ophthalmic element, whereinthe first exterior surface of the ophthalmic element is opposite thesecond exterior surface of the ophthalmic element.

Non-limiting examples of photochromic coatings include coatingscomprising any of the photochromic materials that are discussed above.For example, although not limiting herein, the photochromic coatings canbe photochromic polyurethane coatings, such as those described in U.S.Pat. No. 6,187,444; photochromic aminoplast resin coatings, such asthose described in U.S. Pat. Nos. 4,756,973, 6,432,544B1 and 6,506,488;photochromic polysilane coatings, such as those described in U.S. Pat.No. 4,556,605; photochromic poly(meth)acrylate coatings, such as thosedescribed in U.S. Pat. Nos. 6,602,603, 6,150,430 and 6,025,026, and WIPOPublication WO 01/02449 A2; polyanhydride photochromic coatings, such asthose described in U.S. Pat. No. 6,436,525; photochromic polyacrylamidecoatings such as those described in U.S. Pat. No. 6,060,001;photochromic epoxy resin coatings, such as those described in U.S. Pat.Nos. 4,756,973 and 6,268,055B1; and photochromic poly(urea-urethane)coatings, such as those described in U.S. Pat. No. 6,531,076. Thespecifications of the aforementioned U.S. patents and internationalpublication are hereby specifically incorporated by reference herein.

As used herein the term “transitional coating” means a coating that aidsin creating a gradient in properties between two coatings. For example,although not limiting herein, a transitional coating can aid in creatinga gradient in hardness between a relatively hard coating and arelatively soft coating. Non-limiting examples of transitional coatingsinclude radiation-cured acrylate-based thin films.

Non-limiting examples of protective coatings include abrasion-resistantcoatings comprising organo silanes, abrasion-resistant coatingscomprising radiation-cured acrylate-based thin films, abrasion-resistantcoatings based on inorganic materials such as silica, titania and/orzirconia, organic abrasion-resistant coatings of the type that areultraviolet light curable, oxygen barrier-coatings, UV-shieldingcoatings, and combinations thereof. For example, according to onenon-limiting embodiment, the protective coating can comprise a firstcoating of a radiation-cured acrylate-based thin film and a secondcoating comprising an organo silane. Non-limiting examples of commercialprotective coatings products include SILVUE® 124 and HI-GARD® coatings,available from SDC Coatings, Inc. and PPG Industries, Inc.,respectively.

Another non-limiting embodiment of the present invention provides anophthalmic element comprising at least one orientation facility on atleast a portion of at least one exterior surface of the ophthalmicelement, and an at least partial coating adapted to polarize at leasttransmitted radiation on at least a portion of the at least orientationfacility. As used herein the term “orientation facility” means amechanism that can facilitate the positioning of one or more otherstructures that are exposed to at least a portion of the facility,either directly, indirectly, of a combination, thereof. Non-limitingexamples of orientation facilities that can be used in conjunction withthis and other non-limiting embodiments disclosed herein include atleast partial coatings comprising an at least partially orderedalignment medium, at least partially stretched polymer sheets, at leastpartially treated surfaces, and combinations thereof.

For example, although not limiting herein, according to one non-limitingembodiment, the at least one orientation facility can comprise at leastone at least partial coating comprising an at least partially orderedalignment medium. As used herein the term “alignment medium” means amaterial that can facilitate positioning of one or more other materials.Non-limiting methods of ordering at least a portion of the alignmentmedium are described below in detail.

Non-limiting examples of suitable alignment media that can be used inconjunction with various non-limiting embodiments disclosed hereininclude photo-orientation materials, rubbed-orientation materials, andliquid crystal materials. For example, according one non-limitingembodiment, the at least one orientation facility can comprise at leastone at least partial coating comprising an at least partially orderedalignment medium chosen from photo-orientation materials,rubbed-orientation materials, and liquid crystal materials.

Non-limiting examples of liquid crystal materials suitable for use as analignment medium in accordance with various non-limiting embodimentsdisclosed herein include liquid crystal polymers, liquid crystalpre-polymers, and liquid crystal monomers. For example, according to onenon-limiting embodiment, the at least one orientation facility cancomprise at least one at least partial coating comprising an at leastpartially ordered liquid crystal material chosen from liquid crystalpolymers, liquid crystal pre-polymers, and liquid crystal monomers.

Liquid crystal monomers that are suitable for use as an alignment mediumin conjunction with various non-limiting embodiments disclosed hereininclude mono-functional, as well as multi-functional, liquid crystalmonomers. Further, according to various non-limiting embodimentsdisclosed herein, the liquid crystal monomer can be a cross-linkableliquid crystal monomer, and can further be a photocross-linkable liquidcrystal monomer.

Non-limiting examples of cross-linkable liquid crystal monomers suitablefor use as an alignment medium according to various non-limitingembodiments disclosed herein include liquid crystal monomers havingfunctional groups chosen from acrylates, methacrylates, allyl, allylethers, alkynes, amino, anhydrides, epoxides, hydroxides, isocyanates,blocked isocyanates, siloxanes, thiocyanates, thiols, urea, vinyl, vinylethers, and blends thereof. Non-limiting examples of photocross-linkableliquid crystal monomers suitable for use as an anisotropic materialaccording to various non-limiting embodiments disclosed herein includeliquid crystal monomers having functional groups chosen from acrylates,methacrylates, alkynes, epoxides, thiols, and blends thereof.

Liquid crystal polymers and pre-polymers that are suitable for use as analignment medium in conjunction with various non-limiting embodimentsdisclosed herein include thermotropic liquid crystal polymers andpre-polymers, and lyotropic liquid crystal polymers and pre-polymers.Further, the liquid crystal polymers and pre-polymers can be main-chainpolymers and pre-polymers or side-chain polymers and pre-polymers.Additionally, according to various non-limiting embodiments disclosedherein, the liquid crystal polymer or pre-polymer can be cross-linkable,and further can be photocross-linkable.

Non-limiting examples of liquid crystal polymers and pre-polymers thatare suitable for use as an alignment medium according to variousnon-limiting embodiments disclosed herein include, but are not limitedto, main chain and side chain polymers and pre-polymers havingfunctional groups chosen from acrylates, methacrylates, allyl, allylethers, alkynes, amino, anhydrides, epoxides, hydroxides, isocyanates,blocked isocyanates, siloxanes, thiocyanates, thiols, urea, vinyl, vinylethers, and blends thereof. Non-limiting examples of photocross-linkableliquid crystal polymers and pre-polymers that are suitable for use as analignment medium according to various non-limiting embodiments disclosedherein include those polymers and pre-polymers having functional groupschosen from acrylates, methacrylates, alkynes, epoxides, thiols, andblends thereof.

Non-limiting examples of photo-orientation materials that are suitablefor use as an alignment medium in conjunction with various non-limitingembodiments disclosed include photo-orientable polymer networks.Specific non-limiting examples of suitable photo-orientable polymernetworks include azobenzene derivatives, cinnamic acid derivatives,coumarine derivatives, ferulic acid derivatives, and polyimides. Forexample, according one non-limiting embodiment, the orientation facilitycan comprise at least one at least partial coating comprising an atleast partially ordered photo-orientable polymer network chosen fromazobenzene derivatives, cinnamic acid derivatives, coumarinederivatives, ferulic acid derivatives, and polyimides. Specificnon-limiting examples of cinnamic acid derivatives that can be used asan alignment medium in conjunction with various non-limiting embodimentsdisclosed herein include polyvinyl cinnamate and polyvinyl esters ofparamethoxycinnamic acid.

As used herein the term “rubbed-orientation material” means a materialthat can be at least partially ordered by rubbing at least a portion ofa surface of the material with another suitably textured material. Forexample, although not limiting herein, in one non-limiting embodiment,the rubbed-orientation material can be rubbed with a suitably texturedcloth or velvet. Non-limiting examples of rubbed-orientation materialsthat are suitable for use as an alignment medium in conjunction withvarious non-limiting embodiments disclosed herein include (poly)imides,(poly)siloxanes, (poly)acrylates, and (poly)coumarines. Thus, forexample, although not limiting herein, in one non-limiting embodiment,the at least partial coating comprising the alignment medium can be anat least partial coating comprising a polyimide that has been rubbedwith velvet or a cloth so as to at least partially order at least aportion of the surface of the polyimide.

As discussed above, the at least one orientation facility according tovarious non-limiting embodiments disclosed herein can comprises an atleast partially stretched polymer sheet. For example, although notlimiting herein, a sheet of polyvinyl alcohol (“PVA”) can be at leastpartially stretched, to at least partially order the PVA polymer chains,and there after the sheet can be bonded to the at least a portion of atleast one exterior surface of the ophthalmic element to form theorientation facility.

Further, as discussed above, the at least one orientation facilityaccording various non-limiting embodiments disclosed herein can comprisean at least partially treated surface. As used herein, the term treatedsurface refers to a surface that has been physically altered to impartan order to the surface. Non-limiting examples of at least partiallytreated surfaces include at least partially rubbed surfaces and at leastpartially etched surfaces. For example, according to one non-limitingembodiment, the at least one orientation facility comprises an at leastpartially treated surface chosen from at least partially rubbed surfacesand at least partially etched surfaces.

Non-limiting examples of etched surfaces that are useful in forming theorientation facility according to various non-limiting embodimentsinclude, chemically etched surfaces, plasma etched surfaces, nanoetchedsurfaces (such as surfaces etched using a scanning tunneling microscopeor an atomic force microscope), laser etched surfaces, and electron-beametched surfaces.

Further, according various non-limiting embodiments, the at least oneorientation facility can comprise a first ordered region having a firstgeneral direction and at least one second ordered region adjacent thefirst region having an second general direction that is different fromthe first general direction. Thus, the orientation facility can have aplurality of regions having various arrangements required to form adesired pattern or design. Additionally, as discussed above, one or moredifferent orientation facilities can be combined to form the orientationfacility according to the various non-limiting embodiments disclosedherein.

As previously discussed, according to various non-limiting embodiments,the at least partial coating adapted to polarize at least transmittedradiation can comprise at least one dichroic material. Non-limitingexamples of suitable dichroic materials are set forth above in detail.Further, as previously discussed, it is generally necessary to at leastpartially align at least a portion of the at least one dichroic materialto achieve a net polarization effect. Thus, according to variousnon-limiting embodiments, at least a portion of the at least onedichroic material can be at least partially aligned by direct contactwith at least a portion of the orientation facility or by indirectcontact with at least a portion of the orientation facility, forexample, through one or more other structures or materials.

For example, in one non-limiting embodiment, at least a portion of thedichroic material can be at least partially aligned by direct contactwith at least a portion of at least one orientation facility. Althoughnot limiting herein, according to this non-limiting embodiment at leasta portion of the at least one dichroic material can be at leastpartially aligned such that the long axis of the at least a portion ofthe at least one dichroic material is generally parallel to a generaldirection of at least one ordered region of the orientation facility.Further, although not limiting herein, according to this non-limitingembodiment, the orientation facility can comprise a liquid crystalmaterial.

In another non-limiting embodiment the at least partial coating adaptedto polarize at least transmitted radiation can comprise an anisotropicmaterial and at least one dichroic material. Although not limitingherein, according to this non-limiting embodiment, at least a portion ofthe anisotropic material can be at least partially aligned with the atleast one orientation facility and at least a portion of the at leastone dichroic material can be at least partially aligned with the atleast one at least partially aligned anisotropic material as previouslydiscussed. Suitable non-limiting examples of anisotropic material areset forth above in detail.

Further, in addition to the at least one orientation facility and the atleast partial coating adapted to polarize at least transmittedradiation, according to various non-limiting embodiments disclosedherein, the ophthalmic elements can comprise at least one at leastpartial coating comprising an alignment transfer material, and stillfurther can comprise a plurality of at least partial coatings comprisingan alignment transfer material. As used herein the term “alignmenttransfer material” means a material that can facilitate the propagationof a suitable arrangement or position from one structure or material toanother.

For example, in one non-limiting embodiment, at least one at leastpartial coating comprising an alignment transfer material can be betweenthe at least one orientation facility and the at least a portion of theat least partial coating adapted to polarize at least transmittedradiation. According to this non-limiting embodiment, at least a portionof the alignment transfer material can be aligned with at least aportion of the orientation facility, and at least a portion of the atleast one dichroic material of the at least partial coating can bealigned with the at least a portion of the alignment transfer material.That is, the alignment transfer material can facilitate the propagationof a suitable arrangement or position from the at least one orientationfacility to the at least one dichroic material. Further, if the at leastpartial coating adapted to polarize radiation comprises an anisotropicmaterial, at least a portion of the anisotropic material can be at leastpartially aligned with the alignment transfer material and at least onedichroic material can be at least partially aligned with the at leastone anisotropic material, as discussed above.

Non-limiting examples of alignment transfer materials that are suitablefor use in conjunction with various non-limiting embodiments disclosedherein include liquid crystal materials chosen from liquid crystalpolymers, liquid crystal pre-polymers, and liquid crystal monomer.

Liquid crystal monomers that are suitable for use as alignment transfermaterials in conjunction with various non-limiting embodiments disclosedherein include mono-functional as well as multi-functional liquidcrystal monomers. Further, according to various non-limiting embodimentsdisclosed herein, the liquid crystal monomer can be a cross-linkableliquid crystal monomer, and can further be a photocross-linkable liquidcrystal monomer.

Non-limiting examples of cross-linkable liquid crystal monomers suitablefor use as alignment transfer materials according to variousnon-limiting embodiments disclosed herein include liquid crystalmonomers having functional groups chosen from acrylates, methacrylates,allyl, allyl ethers, alkynes, amino, anhydrides, epoxides, hydroxides,isocyanates, blocked isocyanates, siloxanes, thiocyanates, thiols, urea,vinyl, vinyl ethers and blends thereof. Non-limiting examples ofphotocross-linkable liquid crystal monomers suitable for use asalignment transfer materials according to various non-limitingembodiments disclosed herein include liquid crystal monomers havingfunctional groups chosen from acrylates, methacrylates, alkynes,epoxides, thiols, and blends thereof.

Liquid crystal polymers and pre-polymers that are suitable for usesuitable for use as alignment transfer materials in conjunction withvarious non-limiting embodiments disclosed herein include, but are notlimited to, thermotropic liquid crystal polymers and pre-polymers, andlyotropic liquid crystal polymers and pre-polymers. Further, the liquidcrystal polymers and pre-polymers can be main-chain polymers andpre-polymers or side-chain polymers and pre-polymers. Additionally,according to various non-limiting embodiments disclosed herein, theliquid crystal polymer or pre-polymer can be cross-linkable, and furthercan be photocross-linkable.

Non-limiting examples of liquid crystal polymers and pre-polymers thatare suitable for use as alignment transfer materials according tovarious non-limiting embodiments disclosed herein include, but are notlimited to, main-chain and side-chain polymers and pre-polymers havingfunctional groups chosen from acrylates, methacrylates, allyl, allylethers, alkynes, amino, anhydrides, epoxides, hydroxides, isocyanates,blocked isocyanates, siloxanes, thiocyanates, thiols, urea, vinyl, vinylethers, and blends thereof. Non-limiting examples of photocross-linkableliquid crystal polymers and pre-polymers that are suitable for usealignment transfer materials according to various non-limitingembodiments disclosed herein include those polymers and pre-polymershaving functional groups chosen from acrylates, methacrylates, alkynes,epoxides, thiols, and blends thereof.

Further, the ophthalmic element according to various non-limitingembodiments disclosed herein can comprise one or more coatings that canfacilitate bonding, adhering, or wetting of the at least a portion of atleast one exterior surface of the ophthalmic element by the at least oneorientation facility. For example, the ophthalmic element can furthercomprise an at least partial primer coating positioned between the atleast one orientation facility and the at least a portion of the atleast one exterior surface of the ophthalmic element. Non-limitingexamples of primer coatings that can be suitable for use in conjunctionwith this non-limiting embodiment are discussed above in detail.

Still another non-limiting embodiment provides an ophthalmic elementcomprising at least one at least partial coating comprising an alignmentmedium on at least a portion of at least one exterior surface of theophthalmic element, at least one at least partial coating comprising analignment transfer material on at least a portion of the at least one atleast partial coating comprising the alignment medium, and at least oneat least partial coating comprising an anisotropic material and at leastone dichroic material on at least a portion of the at least one at leastpartial coating comprising the alignment transfer material.

According to various non-limiting embodiments disclosed herein, the atleast partial coating comprising the alignment medium can have anthickness that varies widely depending upon the final application and/orthe processing equipment employed. For example, in one non-limitingembodiment, the thickness of the at least partial coating comprising thealignment medium can range from at least 2 nanometers to 10,000nanometers. In another non-limiting embodiment, the at least partialcoating comprising the alignment medium can have a thickness rangingfrom at least 5 nanometers to 1000 nanometers. In still anothernon-limiting embodiment, the at least partial coating comprising thealignment medium can have a thickness ranging from at least 10nanometers to 100 nanometers. In yet another non-limiting embodiment,the at least partial coating comprising the alignment medium can have athickness ranging from 50 nanometers to 100 nanometers. Additionally,according to various non-limiting embodiments, the ophthalmic elementcan comprise a plurality of at least partial coatings comprising analignment medium. Further each of the plurality of at least partialcoatings can have the same or a different thickness as the other atleast partial coatings of the plurality.

Further, according to various non-limiting embodiments disclosed herein,the at least partial coating comprising the alignment transfer materialcan have a thickness that various widely depending upon the finalapplication and/or the processing equipment employed. For example, inone non-limiting embodiment, the thickness of the at least partialcoating comprising the at least one alignment transfer material canrange from 0.5 microns to 25 microns. In another non-limitingembodiment, the at least partial coating comprising the alignmenttransfer material can have a thickness ranging from 5 to 10 microns.Additionally, according to various non-limiting embodiments, theophthalmic element can comprise a plurality of at least partial coatingscomprising an alignment transfer material. Further each of the pluralityof at least partial coatings can have the same or a different thicknessas the other at least partial coatings of the plurality.

Still further, according to various non-limiting embodiments disclosedherein, the at least partial coating comprising the anisotropic materialand the at least one dichroic material can have a thickness that varieswidely depending upon the final application and/or the processingequipment employed. In one non-limiting embodiment, the at least partialcoating comprising the anisotropic material and the at least onedichroic material can have a thickness of at least 5 microns.Additionally, according to various non-limiting embodiments, theophthalmic element can comprise a plurality of at least partial coatingscomprising an anisotropic material and at least one dichroic material.Further each of the plurality of at least partial coatings can have thesame or a different thickness as the other at least partial coatings ofthe plurality.

As previously discussed, in order to achieve a net polarization effect,at least a portion of the at least one dichroic material generally mustbe brought into suitable arrangement or position (i.e., ordered oraligned). Thus, although not limiting herein, according to variousnon-limiting embodiments, at least a portion of the alignment medium canbe at least partially ordered in a first general direction, at least aportion of the alignment transfer material can be aligned with at leasta portion of the alignment medium in a second general direction that isgenerally parallel to the first general direction, at least a portion ofthe anisotropic material can be at least partially aligned with at leasta portion of the alignment transfer material in a third generaldirection that is generally parallel to the second general direction,and at least a portion of the at least one dichroic material can be atleast partially aligned with at least a portion of the anisotropicmaterial as previously discussed. That is, according to thisnon-limiting embodiment at least a portion of the dichroic material canbe at least partially aligned such that the long axis of the at least aportion of the dichroic material is generally parallel to the thirdgeneral direction of the at least partially aligned anisotropicmaterial.

Further, according to various non-limiting embodiments disclosed herein,the at least partial coating comprising the alignment medium and/or theat least partial coating comprising the alignment transfer material canfurther comprise at least one dichroic material, which can be the sameor different from at least one dichroic material of the at least partialcoating comprising the anisotropic material and the at least onedichroic material. Additionally, any of the at least partial coatingsdiscussed above can further comprise at least one photochromic materialand/or at least one additive that can enhance at least one of theprocessing, the properties, or the performance of the at least partialcoating, or combinations thereof. Non-limiting examples of suitablephotochromic materials and additives are set forth above.

As previously discussed, the ophthalmic element according to variousnon-limiting embodiments disclosed herein can further comprise one ormore coatings that can facilitate bonding, adhering, or wetting of theat least partial coating comprising the alignment medium to or on the atleast a portion of the at least one exterior surface of the ophthalmicelement and/or between two different at least partial coatings. Forexample, according to one non-limiting embodiment, an at least partialprimer coating can be between the at least partial coating comprisingthe alignment medium and the at least a portion of the at least oneexterior surface of the ophthalmic element. In another non-limitingembodiment, an at least partial primer coating can be between the atleast partial coating comprising the alignment medium and the at leastpartial coating comprising the alignment transfer material and/orbetween the at least partial coating comprising the alignment transfermaterial and the at least partial coating comprising the at least oneanisotropic material and the at least one dichroic material. Suitablenon-limiting examples of primer coatings are set forth above in detail.

According to another non-limiting embodiment there is provided an theophthalmic element comprising a substrate, at least one orientationfacility comprising an at least partial coating comprising aphoto-orientable polymer network on at least a portion of at least oneexterior surface of the substrate, and an at least partial coatingadapted to polarize at least transmitted radiation on at least a portionof the at least one at least partial coating comprising thephoto-orientable polymer network. Further, according to thisnon-limiting embodiment, the at least partial coating adapted topolarize radiation comprises a liquid crystal material and at least onedichroic dye.

Additionally, according to the above-mentioned non-limiting embodiment,the at least partial coating comprising the photo-orientable polymernetwork can further comprise at least one dichroic dye, which can be thesame or different from at least one dichroic dye of the at least partialcoating comprising the liquid crystal material and the at least onedichroic dye. Further, any of the at least partial coatings can furthercomprise at least one photochromic material and/or at least one additivethat can enhance at least one of the processing, the properties, or theperformance of the at least partial coating. Non-limiting examples ofsuitable photochromic materials and additives are set forth above.

Further, the ophthalmic element according to this and other non-limitingembodiments disclosed herein can comprise an at least partial coatingcomprising an alignment transfer material between the at least partialcoating comprising the photo-orientable polymer network and the at leastpartial coating adapted to polarize at least transmitted radiation.Non-limiting examples of suitable alignment transfer materials are setforth above.

Additionally, the ophthalmic element according to this non-limitingembodiment can further comprise one or more layers that can facilitatethe at least partial coating comprising the photo-orientable polymernetwork bonding, adhering, or wetting the at least a portion of the atleast one exterior surface of the substrate. For example, according tothis non-limiting embodiment, an at least partial primer coating can bebetween the at least partial coating comprising the photo-orientablepolymer network and the at least a portion of the at least one exteriorsurface of the substrate. Non-limiting examples of primer coatings thatare suitable for use in conjunction with this non-limiting embodimentare set forth above.

Moreover, as discussed above, the ophthalmic element according to thisand other non-limiting embodiments disclosed herein can further compriseat least one additional at least partial coating chosen fromphotochromic coatings, anti-reflective coatings, transitional coatings,primer coatings, and protective coatings on at least a portion of thesubstrate. Non-limiting examples of suitable photochromic coatings,anti-reflective coatings, transitional coatings, primer coatings, andprotective coatings are set forth above.

As previous discussed, embodiments of the present invention contemplateoptical elements and devices. For example, one non-limiting embodimentprovides an optical element comprising an at least partial coatingadapted to polarize at least transmitted radiation on at least a portionof at least one exterior surface of the optical element, the at leastpartial coating comprising an at least partially ordered liquid crystalmaterial and at least one at least partially aligned dichroic material.

Another non-limiting embodiment provides an optical device comprising atleast one optical element comprising an at least partial coatingcomprising an alignment medium on at least a portion of at least oneexterior surface of the at least one optical element, and an at leastpartial coating comprising an anisotropic material and at least onedichroic material on at least a portion of the at least one at leastpartial coating comprising the alignment medium. Further, although notrequired, an at least partial coating comprising an alignment transfermaterial can be between at least a portion of the at least partialcoating comprising the alignment medium and the at least partial coatingcomprising the anisotropic material and the at least one dichroicmaterial. Optical elements, alignment media, alignment transfermaterials, anisotropic materials, and dichroic materials that can beused in conjunction with this non-limiting embodiment are discussedabove in detail.

Additionally, as previously discussed, according to the variousnon-limiting embodiments, the at least partial coating comprising thealignment medium and/or the at least partial coating comprising thealignment transfer material can further comprise at least one dichroicmaterial, which can be the same or different from at least one dichroicmaterial of the at least partial coating comprising the anisotropicmaterial and the at least one dichroic material. Further, any of the atleast partial coatings discussed above can further comprise at least onephotochromic material and/or at least one additive that can enhance atleast one of the processing, the properties, or the performance of theat least partial coating. Non-limiting examples of suitable photochromicmaterials and additives are set forth above.

Moreover, the optical elements according to various non-limitingembodiments disclosed herein can further comprise one or more layersthat can facilitate bonding, adhering, or wetting of any of the coatingsto or on least a portion of the at least one exterior surface of theoptical element. For example, an at least partial primer coating can bebetween the at least partial coating comprising the alignment medium andthe at least a portion of the at least one exterior surface of theoptical element or it can be between the at least partial coatingadapted to polarize at least transmitted radiation and at least aportion the exterior surface of the optical element or another coating.Non-limiting examples of primer coatings that are suitable for use inconjunction with this non-limiting embodiment are set forth above.

Additionally, as discussed above with respect to the foregoingnon-limiting embodiments, optical elements according to thisnon-limiting embodiment can further comprise at least one additional atleast partial coating chosen from photochromic coatings, anti-reflectivecoatings, transitional coatings, primer coatings, and protectivecoatings on at least a portion of the element. Non-limiting examples ofsuitable photochromic coatings, anti-reflective coatings, transitionalcoatings, and protective coatings are set forth above.

Further, although not limiting herein, according to various non-limitingembodiments disclosed herein, the optical device can be chosen fromcorrective and non-corrective eyewear, magnifying eyewear, clips-onlenses attachable to eyewear, and contact lenses.

Various non-limiting embodiments of methods of making polarizing devicesand elements according to the present invention will now be described.One non-limiting embodiment provides a method of making an ophthalmicelement comprising forming an at least partial coating adapted topolarize at least transmitted radiation on at least a portion of atleast one exterior surface of the ophthalmic element.

Although not limiting herein, according this non-limiting embodiment,forming the at least partial coating adapted to polarize at leasttransmitted radiation can comprise applying an at least partial coatingcomprising at least one dichroic material and at least one anisotropicmaterial to at least a portion of at least one exterior surface of theophthalmic element and at least partially aligning at least a portion ofthe at least one dichroic material. As previously discussed, by bringingat least a portion of the at least one dichroic material into suitableposition or arrangement, a net polarization effect can be achieved.Non-limiting examples of dichroic materials and anisotropic materialssuitable for use in conjunction with this and other non-limitingembodiments of methods of making ophthalmic elements disclosed hereinare set forth above.

Non-limiting examples of methods of applying at least partial coatingsthat can be used in conjunction with the methods of making ophthalmicand optical elements according to various non-limiting embodimentsdisclosed herein include, but are not limited to: spin coating, spraycoating, spray and spin coating, curtain coating, flow coating, dipcoating, injection molding, casting, roll coating, wire coating andmethods used in preparing overlays, such as the method of the typedescribed in U.S. Pat. No. 4,873,029. Generally, the application methodselected will depend upon, among other things, the thickness of thedesired coating, the geometry of the surface to which the coating isapplied, and the viscosity of the coating.

Further, according to various non-limiting embodiments disclosed herein,applying the at least partial coating comprising the at least onedichroic material and the at least one anisotropic material can occurbefore, after, or at essentially the same time as at least partiallyaligning at least a portion of the at least one dichroic material.

For example, in one non-limiting embodiment wherein applying the atleast partial coating comprising the at least one dichroic material andthe at least one anisotropic material occurs before at least partiallyaligning at least a portion of the at least one dichroic material, themethod of forming the at least partial coating can comprise spin coatingthe at least partial coating onto at least a portion of at least oneexterior surface of the ophthalmic element. Thereafter, at least aportion of the at least one anisotropic material can be at leastpartially ordered and at least a portion of the at least one dichroicmaterial can be at least partially aligned with the at least partiallyordered anisotropic material, for example by exposing at least a portionof the at least partial coating to at least one orientation facilityafter applying the at least partial coating.

In another non-limiting embodiment, wherein applying the at leastpartial coating comprising the at least one dichroic material and the atleast one anisotropic material occurs at essentially the same time as atleast partially aligning at least a portion of the at least one dichroicmaterial, applying the at least partial coating can comprise coating theat least partial coating onto the at least a portion of the at least oneexterior surface of the ophthalmic element such that, during coating, atleast a portion of the anisotropic material is at least partiallyordered and at least a portion of the at least one dichroic material isat least partially aligned with the at least partially orderedanisotropic material. For example, although not limiting herein, atleast a portion of the anisotropic material can be at least partiallyordered during coating due to the shear forces created by the relativemovement of the exterior surface of the ophthalmic element with respectto the coating being applied. Non-limiting methods of coating accordingto this non-limiting embodiment include, but are not limiting to,curtain coating.

Additionally, according to various non-limiting embodiments disclosedherein, forming the at least partial coating adapted to polarize atleast transmitted radiation can comprise forming a plurality of at leastpartial coatings on the at least a portion of the at least one exteriorsurface of the ophthalmic element, at least one of which is adapted topolarize at least transmitted radiation. For example, although notlimiting herein, according to one non-limiting embodiment forming the atleast partial coating adapted to polarize at least transmitted radiationcan comprise forming a first at least partial coating comprising analignment medium and at least partially ordering at least a portion ofthe alignment medium, forming a second at least partial coatingcomprising an alignment transfer material and at least partiallyaligning at least a portion of the alignment transfer material, andforming a third at least partial coating comprising at least oneanisotropic material and at least one dichroic material and at leastpartially aligning at least a portion of the at least one dichroicmaterial. Additionally, according to this non-limiting embodiment, anyone of the first and second at least partial coatings can furthercomprise at least one dichroic material. Further, any one of the first,second, or third at least partial coatings can comprise at least one ofa photochromic material, and/or an additive that can enhance theprocessing, properties, or performance of the at partial coating.Non-limiting examples of suitable dichroic materials, photochromicmaterials and additives are set forth above in the discussion of thevarious non-limiting embodiments of elements and devices.

The method of making ophthalmic elements according to variousnon-limiting embodiments disclosed herein can further comprise at leastpartially setting at least a portion of one or more of the at leastpartial coatings after forming the at least partial coating on the atleast a portion of the element. As used herein the term “set” means fixin a desired position. For example, in one non-limiting embodiment, atleast a portion of the at least partial coating adapted to polarize atleast transmitted radiation can be at least partially set after formingthe at least partial coating on at least a portion of at least oneexterior surface of the ophthalmic element. Although not limitingherein, according to various non-limiting embodiments disclosed herein,at least partially setting at least a portion of an at least partialcoating can comprise at least one of at least partially curing, at leastpartially cross-linking, or at least partially drying the at least aportion of the at partial coating.

Further, according to various non-limiting embodiments disclosed herein,at least partially setting at least a portion of an at least partialcoating can comprise at least partially curing the at least a portion byexposing the at least a portion of the at least partial coating toinfrared, ultraviolet, gamma or electron radiation so as to initiate thepolymerization reaction of the polymerizable components or cross-linkingwith or without a catalyst or initiator. This can be followed by aheating step, if appropriate.

In one non-limiting embodiment wherein the at least partial coatingcomprises at least one photocross-linkable material, such as aphotocross-linkable liquid crystal material, at least partially settingcan include at least partially cross-linking the photocross-linkablematerial by exposing the material to appropriate actinic radiation. Forexample, although not limiting herein, at least partially setting an atleast partial coating comprising a photocross-linkable material cancomprise exposing at least a portion of the photocross-linkable materialto ultraviolet radiation in an essentially inert atmosphere. As usedherein, the term “essentially inert atmosphere” means an atmospherehaving limited reactivity the material being cured. For example, in onenon-limiting embodiment, the essentially inert atmosphere comprises nogreater than 100 ppm of O₂ gas. Examples of suitable essentially inertatmospheres include, but are not limited to, atmosphere containingnitrogen, argon, and carbon dioxide.

The methods of making the ophthalmic elements according to variousnon-limiting embodiments disclosed herein can further comprise applyingan at least partial primer coating to at least a portion of the at leastone exterior surface of the ophthalmic element prior to applying the atleast partial coating adapted to polarize at least transmittedradiation. Moreover, although not limiting herein, at least oneadditional at least partial coating chosen from photochromic coatings,anti-reflective coatings, transitional coatings, primer coatings, andprotective coatings can be applied to at least a portion of at least oneexterior surface of the ophthalmic element either before or afterapplying the at least partial coating adapted to polarize at leasttransmitted radiation. Non-limiting examples of suitable primercoatings, photochromic coatings, anti-reflective coatings, transitionalcoatings, and protective coatings are described above in detail.

Additionally, if appropriate, the methods according to variousnon-limiting embodiments disclosed herein can further comprise cleaningat least a portion of the ophthalmic element or substrate prior toapplying any coatings thereto. This can be done for the purposes ofcleaning and/or promoting adhesion of the coating. Effective treatmenttechniques for plastics and glass are known to those skilled in the art.

As discussed above, according to one non-limiting embodiment there isprovided a method of making an ophthalmic element comprising forming anat least partial coating adapted to polarize at least transmittedradiation on at least a portion of at least one surface of theophthalmic element. Additionally, according to this non-limitingembodiment, the method can further comprising imparting at least oneorientation facility to the least a portion of the at least one exteriorsurface of the ophthalmic element prior to forming the at least partialcoating adapted to polarize at least transmitted radiation thereon.According to this non-limiting embodiment, imparting the at least oneorientation facility to the at least a portion of the at least oneexterior surface of the ophthalmic element can comprise at least one ofapplying an at least partial coating comprising an alignment medium tothe at least a portion of the at least one exterior surface of theophthalmic element and at least partially ordering at least a portion ofthe alignment medium, applying an at least partially stretched polymersheet to the at least a portion of the at least one exterior surface ofthe ophthalmic element, and at least partially treating at least aportion of the at least one exterior surface of the ophthalmic element,for example, but not limited to, by etching or rubbing.

Still another non-limiting embodiment of a method of making anophthalmic element comprises imparting at least one orientation facilitycomprising an at least partial coating comprising an alignment medium toat least a portion of at least one exterior surface of the ophthalmicelement, applying at least one dichroic material to at least a portionof the at least one orientation facility, and at least partiallyaligning at least a portion of the at least one dichroic material.

According to this non-limiting embodiment, imparting the at least oneorientation facility to the at least a portion of the at least oneexterior surface of the ophthalmic element can comprise applying an atleast partial coating comprising an alignment medium to the at least aportion of the at least one exterior surface of the ophthalmic elementand at least partially ordering at least a portion of the alignmentmedium. For example, although not limiting herein, imparting the atleast one orientation facility can comprise applying an at least partialcoating comprising an alignment medium to at least a portion of at leastone exterior surface of the ophthalmic element and at least partiallyordering at least a portion of the alignment medium. Non-limitingexamples of alignment media that are suitable for use in conjunctionwith the various non-limiting embodiments of methods disclosed hereinare set forth above.

Non-limiting examples of methods of at least partially ordering at leasta portion of the alignment medium that can be used in conjunction withthe methods of making ophthalmic elements according to variousnon-limiting embodiments disclosed herein include at least one ofexposing the at least a portion of the alignment medium toplane-polarized ultraviolet radiation; exposing the at least a portionof the alignment medium to infrared radiation; exposing the at least aportion of the alignment medium to a magnetic field; exposing the atleast a portion of the alignment medium to an electric field; drying theat least a portion of the alignment medium; etching the at least aportion of the alignment medium; exposing the at least a portion of thealignment medium to a shear force; and rubbing the at least a portion ofthe alignment medium.

For example, although not limiting herein, according to one non-limitingembodiment, wherein the alignment medium is a photo-orientation material(such as, but not limited to a photo-orientable polymer network) themethod of making an ophthalmic element can comprise applying an at leastpartial coating comprising a photo-orientation material to at least aportion of at least one exterior surface of the ophthalmic element andat least partially ordering at least a portion of the photo-orientationmaterial by exposing the at least a portion to plane-polarizeultraviolet radiation. Thereafter, the at least one dichroic materialcan be applied to at least a portion of the at least partially orderedphoto-orientation material and at least partially aligned.

Further, if required, imparting the at least one orientation facilitycan further comprise at least partially setting at least a portion ofthe at least one orientation facility. As discussed above, at leastpartially setting can include least partially curing, at least partiallycross-linking, or at least partially drying at least a portion of the atleast one orientation facility. For example, although not limitingherein, the method according to one non-limiting embodiment disclosedherein can comprise imparting at least one orientation facility to atleast a portion of at least one exterior surface of an ophthalmicelement by applying an at least partial coating comprising an alignmentmedium to at least a portion of at least one exterior surface of theophthalmic element, at least partially setting at least a portion of thealignment medium, and at least partially ordering at least a portion ofthe alignment medium prior to applying the at least one dichroicmaterial.

Non-limiting examples of methods of applying the at least one dichroicmaterial to at least a portion of the at least one orientation facilitycomprising the at least partial coating comprising the alignment mediumaccording to the various non-limiting embodiments disclosed hereininclude those methods discussed above for applying at least partialcoatings. For example, although not limiting herein, methods of applyingthe at least one dichroic material can include spin coating, spraycoating, spray and spin coating, curtain coating, flow coating, dipcoating, injection molding, casting, roll coating, wire coating andmethods used in preparing overlays, such as the method of the typedescribed in U.S. Pat. No. 4,873,029.

Additionally, the at least one dichroic material can be applied to atleast a portion of the at least one orientation facility comprising theat least partial coating comprising the alignment medium by imbibing.Suitable imbibition techniques are described, for example, U.S. Pat.Nos. 5,130,353 and 5,185,390, which are specifically incorporated byreference herein. For example, although not limiting herein, thedichroic material can be applied to at least a portion of the at leastone orientation facility by applying the at least one dichroic materialto at least a portion of the orientation facility, either as the neatdichroic material or dissolved in a polymeric or other organic solventcarrier, and then subjecting the dichroic material and the orientationfacility to heat to cause the at least one dichroic material to diffuseinto at least a portion of the orientation facility.

Further, according to various non-limiting embodiments disclosed herein,applying the at least one dichroic material to at least a portion of theat least one orientation facility can occur before aligning the at leastone dichroic material, after aligning the at least one dichroicmaterial, or at essentially the same time as aligning the at least onedichroic material. For example, although not limiting herein, in onenon-limiting embodiment, the at least one dichroic material can beapplied prior to aligning by spin coating on a solution or mixture ofthe at least one dichroic material and a liquid crystal polymer in acarrier onto the at least a portion of the orientation facility, andthereafter evaporating at least a portion of the solvent or carrier toalign at least a portion of the liquid crystal polymer and at least aportion of the at least one dichroic material. In another non-limitingembodiment, the at least one dichroic material can be applied andaligned at essentially the same time, for example, by imbibing at leasta portion of the orientation facility with the at least one dichroicmaterial. Methods of imbibing are discussed above in detail.

According to various non-limiting embodiments disclosed herein, the atleast one dichroic material can be applied to the at least oneorientation facility as a solution or mixture with a carrier, ortogether with one or more other materials, such as anisotropicmaterials, photochromic materials, and additives that can improve atleast one of the processing, properties, or performance of the materialapplied. Non-limiting examples of suitable anisotropic materials,photochromic materials, and additives are set forth with respect to thevarious non-limiting embodiments of elements and devices discussedabove.

Additionally, the methods of making ophthalmic elements according tovarious non-limiting embodiments disclosed herein can further compriseapplying an at least partial primer coating to the at least a portion ofthe at least one exterior surface of the ophthalmic element prior toimparting the at least one orientation facility to the at least aportion of the exterior surface. Moreover, at least one additional atleast partial coating chosen from photochromic coatings, anti-reflectivecoatings, transitional coatings, primer coatings, and protectivecoatings can be applied to at least a portion of at least one exteriorsurface of the ophthalmic element and/or over at least a portion of theat least one dichroic material. Non-limiting examples of suitable primercoatings, photochromic coatings, anti-reflective coatings, transitionalcoatings, and protective coatings are all described above.

Another non-limiting embodiment provides a method of making anophthalmic element comprising applying an at least partial coating to atleast a portion of at least one exterior surface of the ophthalmicelement and adapting at least a portion of the at least partial coatingto polarize at least transmitted radiation. According to thisnon-limiting embodiment, applying the at least partial coating to the atleast a portion of the at least one exterior surface of the ophthalmicelement can occur before, after, or at essentially the same time asadapting the at least a portion of the at least partial coating topolarize at least transmitted radiation.

For example, although not limiting herein, according to one non-limitingembodiment, applying the at least partial coating to the at least aportion of the at least one exterior surface of the ophthalmic elementcan comprise applying an at least partial coating comprising ananisotropic material and at least one dichroic material to the at leasta portion of the at least one exterior surface; and adapting at least aportion of the at least partial coating to polarize at least transmittedradiation can comprise at least partially aligning at least a portion ofthe at least one dichroic material. Further, at least partially aligningat least a portion of the at least one dichroic material can comprise atleast partially ordering at least a portion of the anisotropic materialand at least partially aligning the at least one dichroic material withat least a portion of the at least partially ordered anisotropicmaterial.

Suitable methods of at least partially ordering at least a portion ofthe anisotropic material include, but are not limited to, at least oneexposing of the anisotropic material to plane-polarized ultravioletradiation, exposing the at least a portion of the anisotropic materialto infrared radiation, exposing the at least a portion of theanisotropic material to a magnetic field, exposing the at least aportion of the anisotropic material to an electric field, drying the atleast a portion of the anisotropic material, etching the at least aportion of the anisotropic material, exposing the at least a portion ofthe anisotropic material to a shear force, rubbing the at least aportion of the anisotropic material, and aligning at least a portion ofthe anisotropic material with another structure or material, such as,but not limited to, an at least partially ordered alignment medium.

In another non-limiting embodiment, applying the at least partialcoating to the at least a portion of at least one exterior surface ofthe ophthalmic element comprises applying an at least partial coatingcomprising an alignment medium to the at least a portion of the at leastone exterior surface of the ophthalmic element, and adapting at least aportion of the at least partial coating to polarize at least transmittedradiation comprises at least partially ordering at least a portion ofthe alignment medium, applying at least one dichroic material to atleast a portion of the at least partial coating comprising the alignmentmedium, and at least partially aligning at least a portion of the atleast one dichroic material.

Non-limiting examples of alignment media that are suitable for use inconjunction with various non-limiting embodiments of methods disclosedherein include those alignment media previous described with respect tothe various non-limiting embodiments discussed above. For example,according to one non-limiting embodiment, wherein applying the at leastpartial coating to the at least a portion of at least one exteriorsurface of the ophthalmic element comprises applying an at least partialcoating comprising an alignment medium to the at least a portion of theat least one exterior surface of the ophthalmic element, the alignmentmedium can be chosen from photo-orientation materials,rubbed-orientation materials, and liquid crystal materials.

Further according to various non-limiting embodiments at least partiallyordering at least a portion of the alignment medium can comprise atleast one exposing of the alignment medium to plane-polarizedultraviolet radiation, exposing the at least a portion of the alignmentmedium to infrared radiation, exposing the at least a portion of thealignment medium to a magnetic field, exposing the at least a portion ofthe alignment medium to an electric field, drying the at least a portionof the alignment medium, etching the at least a portion of the alignmentmedium, exposing the at least a portion of the alignment medium to ashear force, and rubbing the at least a portion of the alignment medium.

For example, although not limiting herein, according to one non-limitingembodiment wherein the alignment medium is a photo-orientation material(such as, but not limited to, a photo-orientable polymer network), atleast partially ordering at least a portion of the photo-orientationmaterial can comprise exposing at least a portion of thephoto-orientation material to plane-polarized ultraviolet radiation.

Further, according to certain non-limiting embodiments wherein adaptingat least a portion of the at least partial coating to polarize at leasttransmitted radiation comprises applying at least one dichroic materialto at least a portion of the at least partial coating comprising an atleast partially ordered alignment medium and at least partially aligningat least a portion of the at least one dichroic material, applying theat least one dichroic material can occur before, after, or atessentially the same time as at least partially aligning at least aportion of the at least one dichroic material. Non-limiting methods ofapplying the at least one dichroic material to the at least a portion ofthe at least partial coating comprising the alignment medium includespin coating, spray coating, spray and spin coating, curtain coating,flow coating, dip coating, injection molding, casting, roll coating,wire coating and methods used in preparing overlays, such as the methodof the type described in U.S. Pat. No. 4,873,029, and imbibing.

The methods of making the ophthalmic elements according to variousnon-limiting embodiments disclosed herein can further comprise applyingan at least partial primer coating to at least a portion of the at leastone exterior surface of the ophthalmic element prior to forming andadapting the at least partial coating to polarize at least transmittedradiation. Additionally, the methods of making the ophthalmic elementscan further comprise applying at least one additional at least partialcoating chosen from photochromic coatings, anti-reflective coatings,transitional coatings, primer coatings, and protective coatings to atleast a portion of the ophthalmic elements. For example, although notlimiting herein, the at least one additional at least partial coatingcan be applied over at least a portion of the at least partial coatingthat is adapted to polarize at least transmitted radiation.Alternatively, or additionally, the at least partial coating adapted topolarize at least transmitted radiation can be formed on at least aportion of a first exterior surface of the ophthalmic element and the atleast one additional at least partial coating can be applied to at leasta portion of a second exterior surface of the ophthalmic element,wherein the first exterior surface of the ophthalmic element is oppositethe second exterior surface of the ophthalmic element. Non-limitingexamples of such coatings are described above in detail.

Another non-limiting embodiment of a method of making an ophthalmicelement comprises applying an at least partial coating comprising analignment medium to at least a portion of at least one exterior surfaceof the ophthalmic element and at least partially ordering at least aportion of the alignment medium. Thereafter, according to thisnon-limiting embodiment, an at least partial coating comprising ananisotropic material and at least one dichroic material is applied to atleast a portion of at least partial coating comprising the alignmentmedium and at least a portion of the at least one dichroic material isat least partially aligned. Although not required, at least one at leastpartial coating comprising an alignment transfer material can be appliedto at least a portion of the at least partial coating comprising thealignment medium and at least partially aligning prior to applying theat least partial coating comprising the anisotropic material and the atleast one dichroic material thereto.

According to this non-limiting embodiment, at least partially orderingat least a portion of the alignment medium can comprise at least one ofexposing the at least a portion of the alignment medium toplane-polarized ultraviolet radiation, exposing the at least a portionof the alignment medium to infrared radiation, exposing the at least aportion of the alignment medium to a magnetic field, exposing the atleast a portion of the alignment medium to an electric field, drying theat least a portion of the alignment medium, etching the at least aportion of the alignment mediums, exposing the at least a portion thealignment medium to a shear force, and rubbing the at least a portion ofthe alignment medium.

Further, although not limiting herein, as previously discussed, any ofthe at least partial coatings described above can be at least partiallyset after being applied. For example, according to one non-limitingembodiment, at least a portion of the at least partial coatingcomprising the alignment medium can be at least partially set prior,during, or after at least partially ordering the at least a portion ofthe alignment medium. Further, according to this non-limitingembodiment, at least a portion of the at least partial coatingcomprising the alignment transfer material and/or the at least partialcoating comprising the anisotropic material and the at least onedichroic material can be at least partially set by curing at least aportion of the at least partial coating. For example, at least a portionof the alignment transfer material can be exposed to ultravioletradiation under an inert atmosphere to cure the at least a portion ofthe alignment transfer material. Similarly, at least a portion of the atleast partial coating comprising the anisotropic material and the atleast one dichroic material can be cured by exposing at least a portionof the anisotropic material to ultraviolet radiation under an inertatmosphere after at least partially aligning at least a portion of theat least one dichroic material.

Another non-limiting embodiment of the invention provides a method ofmaking a lens for ophthalmic applications comprising applying an atleast partial coating comprising a photo-orientable polymer network toat least a portion of at least one exterior surface of the lens, atleast partially ordering at least a portion of the photo-orientablepolymer network with plane-polarized ultraviolet radiation. Thereafter,an at least partial coating comprising a liquid crystal material and atleast one dichroic dye is applied to at least a portion of the at leastpartial coating comprising the photo-orientable polymer network and theat least one dichroic dye is at least partially aligned. After aligningthe at least a portion of the coating comprising the liquid crystalmaterial and the at least one dichroic dye, at least a portion of thecoating comprising the liquid crystal material and the at least onedichroic dye can be at least partially set, for example although notlimiting herein, by curing. Although not required, an at least partialcoating comprising an alignment transfer material can be applied to atleast a portion of the at least partial coating comprising thephoto-orientable polymer network prior to applying the at least partialcoating comprising the liquid crystal material and the at least onedichroic dye thereto.

Other embodiments of the invention provide methods of making an opticalelement comprising applying an at least partial coating to at least aportion of at least one exterior surface of the optical element, andadapting at least a portion of the at least partial coating to polarizeradiation. Suitable methods of applying an at least partial coating andadapting at least a portion of the at least partial coating to polarizeradiation are described above in detail.

Various non-limiting embodiments of the present invention will now beillustrated in the following, non-limiting examples.

EXAMPLES Step 1 Preparation of Solutions of Anisotropic Materials

To a beaker containing a magnetic stir bar and positioned on a magneticstirrer was added 3 grams of each of the following liquid crystalmonomers (“LCM”), which are available from EMD Chemicals, Inc., in theorder listed with stirring:

-   -   RM 23—reported to have the molecular formula of C₂₃H₂₃NO₅    -   RM 257—reported to have the molecular formula of C₃₃H₃₂O₁₀    -   RM 82—reported to have the molecular formula of C₃₉H₄₄O₁₀    -   RM 105—reported to have the molecular formula of C₂₃H₂₆O₆

Anisole (8.0 grams) was added to the contents in the beaker and theresulting mixture was heated to 60° C. and stirred until the solids weredissolved as determined by visual observation. The resulting liquidcrystal monomer solutions (or “LCMS”) were divided into two portions,“Portion A-LCMS” and “Portion B-LCMS.” A beaker containing PortionA-LCMS was placed uncovered in a fume hood on a balance until thepercent solids increased from the initial 60 percent to 62 percent.Portion B-LCMS had 60 percent solids.

Step 2 Preparation of Stock Solutions of Anisotropic Materials andDichroic Materials

The following three dichroic dyes, which are available from MitsubishiChemical, were used to prepare individual dichroic dye-colored liquidcrystal monomer solutions (i.e., Red-, Blue-, Yellow-or Gray-LCMS):

-   -   LSR-652 reported to be a red dye of Lot: 01J0315;    -   LSR-335 reported to be a blue dye of Lot: 01C131; and    -   LSR-120 reported to be a yellow dye of Lot: 2D231.

Each of the Red-LCMS, Blue-LCMS, and Yellow-LCMS was prepared by addingto the Portion A-LCMS (prepared in Step 1) the amount of dichroic dyenecessary to produce a dichroic dye-colored LCMS having the percentdichroic dye, based on the solids of the Portion A-LCMS, listed for eachbelow. The Gray-LCMS was prepared using Portion B-LCMS from Step 1 andadding to it the combination of dichroic dyes listed below in theamounts necessary to result in the percent dye, based on the solids ofPortion B-LCMS, listed below. Dye-Colored LCMS Dichroic Dye PercentDichroic Dye Red-LCMS LSR652 2.0 Blue-LCMS LSR335 3.0 Yellow-LCMS LSR1202.5 Gray-LCMS LSR652 0.8 LSR335 1.1 LSR120 0.6

The individual Red-LCMS, Blue-LCMS and Yellow-LCMS also contained 1.0percent, based on the solids of Portion A-LCM, of Irgacure 819, aphotoinitiator that is available from Ciba-Geigy Corporation; and 0.5percent, based on the solids of Portion A-LCMS, of a combination ofstabilizers in a 50:50 weight ratio. The stabilizers were TINUVIN-292, alight stabilizer for coatings from Ciba-Geigy, and SANDUVOR VSU, a lightstabilizer based on oxalanilide chemistry available from Clariant. TheGray-LCMS contained 1.0 percent, based on the solids of Portion B-LCMS,each of Irgacure 819 and the aforementioned combination of stabilizers.

Step 3: Preparation of Coating Solutions Comprising AnisotropicMaterials and Dichroic Materials

Coating solutions comprising anisotropic materials and dichroicmaterials were prepared by adding the stock dichroic dye-colored LCMSfrom Step 2, in the amounts indicated, as weighed on an analyticalbalance, in the following Examples 1-5 to a beaker and mixing withheating to 50-60° C., if necessary, to prevent the liquid crystalmonomer from precipitating and to dissolve the dye. An additionalcoating solution, Example 6, used the Gray-LCMS prepared above in Step2, and was also heated with mixing as required. After mixing, each ofthe solutions were filtered using a syringe filter having a pore size of1.2 microns to remove any particulate matter.

Example 1

Weight of Material Material (grams) Red Dye Solution 0.6008 Blue DyeSolution 1.2772 Yellow Dye Solution 0.5049

Example 2

Weight of Material Material (grams) Red Dye Solution 0.5415 Blue DyeSolution 0.8892 Yellow Dye Solution 0.3501

Example 3

Material Weight (grams) Red Dye Solution 0.5410 Blue Dye Solution 0.8880Yellow Dye Solution 0.3945

Example 4

Material Weight (grams) Red Dye Solution 0.3939 Blue Dye Solution 0.6460Yellow Dye Solution 0.3272

Example 5

Material Weight (grams) Red Dye Solution 0.3758 Blue Dye Solution 0.4908Yellow Dye Solution 0.2832

Each of the aforementioned coating solutions were used in the proceduredescribed hereinafter in Parts A-D, to prepare at least partial coatingsadapted to polarize at least transmitted radiation on the surface asubstrate. After preparation, the absorption ratio of each of the coatedsubstrates was measured in the Absorption Ratio Measurement Testdescribed in Part E.

Part A Substrate Cleaning

Square substrates measuring 2 inches by 2 inches by 0.25 inch (5.08 cmby 5.08 cm by 0.635 cm) were obtained from following: CR-39® monomer orTRIVEX® 151 lens material, both of which are available from PPGIndustries, Inc.; 70 mm diameter plano lenses of CR-607® monomer, whichis available from PPG Industries, Inc.; and photochromic lenses formTransitions Optical Incorporated with a refractive index of 1.50.Thereafter, each substrate was cleaned by washing in a solution ofliquid soap and water, rinsing with deionized water, and rinsing withisopropyl alcohol. After washing and rinsing, the substrates were driedand treated with oxygen plasma at a flow rate of 100 milliliters (mL)per minute of oxygen at 100 watts of power for one minute.

As indicated in Part D and Table 1 below, some of the substrates werefurther treated with the a primer coating described in U.S. Pat. No.6,150,430. More specifically, these substrates were treated bydispensing the primer coating composition for 10 seconds to thesubstrates while the substrate was spinning at 1500 rpm. The coatedsubstrates were then cured in a Light-Welder® 5000-EC UV light sourcefrom Dymax Corp., at a distance of 4 inches from the light for 10seconds.

Part B Preparation of Orientation Facility Using a Photo-OrientablePolymer Network

An orientation facility was imparted to a portion of the cleanedsubstrates (described in Part A above) as follows. A solution of aphoto-orientable polymer network available as Staralign® 2200 CP2 or CP4solution, which designations are reported to mean 2 weight percent incyclopentane and 4 weight percent in cyclopentane, respectively, fromHuntsman Advanced Materials, was applied on a portion of the surface ofthe substrate prepared in Part A by dispensing the Staralign solutionfor 2 to 3 seconds onto the substrate. As the Staralign solution wasdispensed onto the substrate, the substrate was spun at 600 to 800revolutions per minute for about 2 to 3 minutes. After coating, thesubstrates were placed in an oven maintained at 130° C. for 20 to 30minutes. With reference to Table 1 below, the Staralign 2200 CP2solution was used on Samples 6A1 and 6A2. All others samples, except6A(magnetic) were coated with the Staralign 2200 CP4.

At least a portion of the photo-orientable polymer network was at leastpartially ordered by exposure to plane-polarized ultraviolet radiation,at a peak intensity of 18 milliWatts/cm² of UVA (320-390 nm) as measuredusing a UV Power Puck™ electro-optic radiometer from ElectronicInstrumentation and Technology, Inc. The source of the ultravioletradiation was a BLAK-RAY Model B-100A Longwave UV Lamp. Again, withreference to Table 1, Samples 1A to 6D, were exposed to theplane-polarized ultraviolet radiation for 2 minutes, Samples 6A1 and 6A2were exposed to the plane-polarized ultraviolet radiation for 3 minutes.

Part C Preparation of at Least Partial Coatings Adapted to Polarize atLeast Transmitted Radiation

At least partial coatings adapted to polarize at least transmittedradiation were then formed on each of the substrates prepared in Part Busing one of the dichroic dye-colored LCMS described above in Examples1-6 of Step 3.

The dichroic dye-colored LCMS was applied to at least a portion of theorientation facility on the surface of the substrate by spin coating.More specifically, approximately 1 mL of the dichroic dye-colored LCMSwas dispensed onto the substrate and the excess dichroic dye-coloredLCMS, if any, was drained off. Thereafter, the substrate was spun at 300to 400 revolutions per minute for 4 to 6 minutes. After spin coating,the substrate was placed in a 45° C. to 55° C. oven for 20 to 40 minutesto permit at least a portion of the LCM and at least a portion of thedichroic dye to align.

Thereafter, the resultant coatings were tested for alignment using twocross-polarized polarizing films (#45669) from Edmund Industrial Optics.Each coated substrate was positioned between the cross-polarizedpolarizing films so that the coated substrate was parallel with at leastone of the films such that the visible light transmitted through theconfiguration of the polarizing films and the coated substrate wasreduced. At least partial alignment was verified by observing anincrease in the transmitted visible light when one of the polarizingfilms was rotated 45 degrees clockwise or counterclockwise while viewinga visible light source through the configuration. When two at leastpartial coatings of the dichroic dye colored-LCMS were applied, theaforementioned steps of this Part C were completed prior to theapplication of the second at least partial coating.

After verifying at least partial alignment of the coatings, the at leastpartial coatings were further cured by covering each of the coatedsubstrates with a 6-base polycarbonate plano lens having a diameter of70 mm and thickness of 2.0 mm so that it was about 1 mm to 2 mm abovethe surface of the coated substrate. The resulting polycarbonatelens/coated substrate assembly was placed on an ultraviolet conveyorcuring line obtained from Eye Ultraviolet, Inc. The UV conveyor curingline had a nitrogen atmosphere in which the oxygen level was less than100 ppm. The conveyor traveled three feet per minute beneath twoultraviolet “type D” 400 watt/inch iron iodide doped mercury lamps of 10inches in length. One of the lamps was positioned 2.5 inches above theconveyor and the other lamp was positioned 6.5 inches above theconveyor. The peak intensity of different ultraviolet wavelengthsprovided by the ultraviolet conveyor curing line was measured using a UVPower Puck™ electro-optic radiometer, described hereinbefore. The peakintensity of UVA (320 to 390 nm) measured was 0.239 Watts/cm² and of UVV(395 to 445 nm) measured was 0.416 Watts/cm².

Part D Preparation of at Least Partial Coatings Adapted to Polarize atLeast Transmitted Radiation Using a Magnetic Field

The square substrates of polymerizates of CR39® monomer lens materialcoated with the primer coatings as described in Part A were used toprepare coated samples in this Part D. However, as described below, thesubstrates were not prepared according to Part B prior to coating withthe Gray-LCMS.

For the samples prepared according to this Part D, the procedure of PartC was generally followed to coat the primer-coated substrates (describedin above in Part A) with the Gray-LCMS of Example 6 (described above inStep 3), except prior to curing the coated substrate, at least a portionof the coating was at least partially ordered as follows. The coatedsubstrate was placed on a temperature controlled hot plate 8 inchesbeneath a temperature controlled infrared lamp and between the North andSouth poles of a 0.35 Tesla magnet that were separated by a distance of11 centimeters. Both temperature controllers were set to maintain atemperature of from approximately 55° C. to 60° C. The coated substratewas kept under these conditions for 40 to 45 minutes to at leastpartially order the LCM and the dichroic dye. Thereafter, the orderedcoating was cured and the ordering of the coating was verified asdescribed in Part C (with respect to the aligned coatings). Theresulting sample is identified as 6A(Magnetic) in Table 1.

Part E Absorption Ratio Measurement Tests

Absorption ratios for each coated substrates were determined as follows.A CARY 4000 UV-Visible spectrophotometer was equipped with aself-centering sample holder having a polarizer analyzer (MoxtekProFlux™ polarizer). The instrument was set with the followingparameters: Scan speed=600 nm/min; Data interval=1.0 nm; Integrationtime=100 ms; Absorbance range=0-6.5; Y mode=absorbance;X-mode=nanometers and the scanning range was 400 to 800 nm. Options wereset for 3.5 SBW (slit band width), and double for beam mode. Baselineoptions were set for Zero/baseline correction. A sample of eachsubstrate material without the orientation facility and/or the coatingadapted to polarize at least transmitted radiation were used to set theZero/Baseline correction. For the samples wherein the substrate wascoated with a primer coating, the Zero/Baseline correction was set usingthe primer-coated substrate. Also, 2.5 Neutral Density filters were inthe reference path for all scans. The coated substrate samples weretested in air, at room temperature (73° F.±5° F.) maintained by the labair conditioning system.

Orientation of the sample polarizer to be parallel and perpendicular tothe analyzer polarizer was accomplished in the following manner. TheCary 4000 was set to 500 nm (or at a peak absorbance of the sample), andthe absorbance was monitored as the sample was rotated in smallincrements (1 to 5 degrees). The rotation of the sample was continueduntil the absorbance was maximized. This position was defined as theperpendicular or 90 degree position. The parallel position was obtainedby rotating the stage 90 degrees clock-wise or counter-clockwise.

The absorption spectra was collected at both 90 and 0 degrees for eachsample. Data analysis was handled with the Igor Pro software availablefrom WaveMetrics. The spectra were loaded into Igor Pro and theabsorbances were used to calculate the absorption ratios at 566 nm. Thecalculated absorption ratios are listed in Table 1.

In Table 1, the sample numbers correspond to the coating composition(e.g., Examples 1-6) applied to the substrate tested. Differentalphabetic letters associated with the sample number denote differentsubstrates as follows: “A” denotes a polymerizate of CR39® monomer; “B”denotes a polymerizate of TRIVEX® 151 lens material; “C” denotes thephotochromic lenses from Transition Optical Incorporated having arefractive index of 1.50; and “D” denotes a polymerizate of CR-607®monomer. Double letters indicate that the substrate was coated twice inPart C. The results for Samples 6A1 and 6A2 were arithmetic averages of2 results. The results for the other samples were of single coatedsubstrates tested. TABLE 1 Sample Primer Coating Number PresentAbsorption Ratio 1A − 3.1 2A − 5.7 3A − 2.4 4A − 4.0 5A − 5.4 6A − 2.66AA − 4.4 6B − 3.0 6C − 3.1 6D − 3.9 6A1 + 6.2 6A2 − 7.0 6A + 5.4(Magnetic)

As indicated in Table 1, the at least partial coatings adapted topolarize at least transmitted radiation according to the non-limitingexamples described above exhibited absorption ratios ranging from 2.4 to7.0.

It is to be understood that the present description illustrates aspectsof the invention relevant to a clear understanding of the invention.Certain aspects of the invention that would be apparent to those ofordinary skill in the art and that, therefore, would not facilitate abetter understanding of the invention have not been presented in orderto simplify the present description. Although the present invention hasbeen described in connection with certain embodiments, the presentinvention is not limited to the particular embodiments disclosed, but isintended to cover modifications that are within the spirit and scope ofthe invention, as defined by the appended claims.

1-75. (canceled)
 76. An ophthalmic element comprising: at least one atleast partial coating comprising an alignment medium on at least aportion of at least one exterior surface of the ophthalmic element; atleast one at least partial coating comprising an alignment transfermaterial on at least a portion of the at least one at least partialcoating comprising the alignment medium; and at least one at leastpartial coating comprising an anisotropic material and at least onedichroic material on at least a portion of the at least one at leastpartial coating comprising the alignment transfer material.
 77. Theophthalmic element of claim 76 wherein at least a portion of thealignment medium is at least partially ordered in a first generaldirection, at least a portion of the alignment transfer material is atleast partially aligned in a second general direction that is generallyparallel to the first general direction, at least a portion of theanisotropic material is at least partially aligned in a third generaldirection that is generally parallel to the second general direction,and at least a portion of the at least one dichroic material is at leastpartially aligned with at least a portion of the anisotropic materialsuch that a long axis of the at least a portion of the at least onedichroic material is generally parallel to the third general directionof the at least partially aligned anisotropic material.
 78. Theophthalmic element of claim 76 wherein the alignment medium is chosenfrom photo-orientation materials, rubbed-orientation materials, andliquid crystal materials. 79-87. (canceled)
 88. The ophthalmic elementof claim 76 wherein the alignment transfer material is a liquid crystalmaterial chosen from liquid crystal polymers, liquid crystalpre-polymers, and liquid crystal monomers. 89-91. (canceled)
 92. Theophthalmic element of claim 76 wherein at least one at least partialcoatings comprising the alignment transfer material has an averagethickness ranging from 0.5 microns to 25 microns.
 93. The ophthalmicelement of claim 76 wherein at least one at least partial coatingscomprising the alignment transfer material has an average thicknessranging from 5 microns to 10 microns. 94-95. (canceled)
 96. Theophthalmic element of claim 76 wherein at least one at least partialcoating comprising the anisotropic material and at least one dichroicmaterial has an average thickness of at least 5 microns. 97-103.(canceled)
 104. The ophthalmic element of claim 76 wherein theanisotropic material is a liquid crystal material chosen from liquidcrystal polymers, liquid crystal pre-polymers, and liquid crystalmonomers.
 105. The ophthalmic element of claim 76 wherein theanisotropic material is a liquid crystal material having at least onefunctional group chosen from acrylates, methacrylates, allyl, allylethers, alkynes, amino, anhydrides, epoxides, hydroxides, isocyanates,blocked isocyanates, siloxanes, thiocyanates, thiols, urea, vinyl, andvinyl ethers. 106-108. (canceled)
 109. The ophthalmic element of claim76 further comprising at least one at least partial primer coatingbetween at least a portion of the at least one at least partial coatingcomprising an alignment medium and the at least a portion of the atleast one exterior surface of the ophthalmic element.
 110. Theophthalmic element of claim 76 further comprising at least oneadditional at least partial coating chosen from photochromic coatings,anti-reflective coatings, transitional coatings, primer coatings, andprotective coatings on at least a portion of the ophthalmic element.111-177. (canceled)
 178. A method of making an ophthalmic elementcomprising: applying an at least partial coating comprising an alignmentmedium to at least a portion of at least one exterior surface of theophthalmic element; at least partially ordering at least a portion ofthe alignment medium; applying an at least partial coating comprising ananisotropic material and at least one dichroic material to at least aportion of the at least partial coating comprising the at leastpartially ordered alignment medium; and at least partially aligning atleast a portion of the at least one dichroic material.
 179. The methodof claim 178 wherein at least partially ordering at least a portion ofthe alignment medium comprises at least one of exposing the at least aportion of the alignment medium to plane-polarized ultravioletradiation, exposing the at least a portion of the alignment medium toinfrared radiation, exposing the at least a portion of the alignmentmedium to a magnetic field, exposing the at least a portion of thealignment medium to an electric field, drying the at least a portion ofthe alignment medium, etching the at least a portion of the alignmentmedium, exposing the at least a portion of the alignment medium to ashear force, and rubbing the at least a portion of the alignment medium.180-194. (canceled)
 195. The ophthalmic element of claim 76 wherein theat least one at least partial coating comprising the alignment mediumfurther comprises at least one of a dichroic material, a photochromicmaterial, a dye, an alignment promoter, a kinetic enhancing additive, aphotoinitiator, a solvent, a light stabilizer, a heat stabilizer, a moldrelease agent, a rheology control agent, a leveling agent, a freeradical scavenger, and an adhesion promoter.
 196. The ophthalmic elementof claim 76 wherein the at least one at least partial coating comprisingthe alignment transfer material further comprises at least one of adichroic material, a photochromic material, a dye, an alignmentpromoter, a kinetic enhancing additive, a photoinitiator, a solvent, alight stabilizer, a heat stabilizer, a mold release agent, a rheologycontrol agent, a leveling agent, a free radical scavenger, and anadhesion promoter.
 197. The ophthalmic element of claim 76 wherein theat least one dichroic material is chosen from polymerizable dichroicmaterials, azomethines, indigoids, thioindigoids, merocyanines, indans,quinophthalonic dyes, perylenes, phthaloperines, triphenodioxazines,indoloquinoxalines, imidazo-triazines, tetrazines, azo and (poly)azodyes, benzoquinones, naphthoquinones, anthraquinone and(poly)anthraquinones, anthrapyrimidinones, iodine and iodates.
 198. Theophthalmic element of claim 76 wherein the at least one at least partialcoating comprising the anisotropic material and at least one dichroicmaterial further comprises at least one of a photochromic material, adye, an alignment promoter, a kinetic enhancing additive, aphotoinitiator, a solvent, a light stabilizer, a heat stabilizer, a moldrelease agent, a rheology control agent, a leveling agent, a freeradical scavenger, and an adhesion promoter.
 199. The method of claim178 wherein applying the at least partial coating comprising theanisotropic material and at least one dichroic material to the at leasta portion of the at least partial coating comprising the at leastpartially ordered alignment medium comprises: applying a mixture of ananisotropic material and at least one dichroic material to the at leasta portion of the at least partial coating comprising the at leastpartially ordered alignment medium; and wherein at least partiallyaligning at least a portion of the at least one dichroic materialcomprises: at least partially aligning at least a portion of theanisotropic material with at least a portion of the at least partialcoating comprising the at least partially ordered alignment medium, andat least partially aligning at least a portion of the at least onedichroic material with at least a portion of the at least partiallyaligned portion of the anisotropic material.
 200. The method of claim199 further comprising at least partially setting at least a portion ofthe at least partial coating comprising the anisotropic material and theat least one dichroic material after at least partially aligning atleast a portion of the at least one dichroic material.
 201. Anophthalmic element comprising: at least one at least partial coatingcomprising an at least partially ordered alignment medium on at least aportion of at least one exterior surface of the ophthalmic element; andat least one at least partial coating comprising at least one at leastpartially aligned anisotropic material and at least one at leastpartially aligned dichroic material on at least a portion of the atleast one at least partial coating comprising the at least partiallyordered alignment medium.